Benzenesulphonamide derivatives as herbicides or desiccant/defoliant compounds

ABSTRACT

The present invention relates to benzenesulfonamide derivatives of the formula I  
                 
in which the variables are as defined below: 
         X 1  is hydrogen or halogen;    X 2  is hydrogen, cyano, CS—NH 2 , halogen, alkyl or haloalkyl;    X 3  is hydrogen, cyano, alkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl or phenylalkyl, where the phenyl radical for its part may be substituted;    Y is a group —C(A)B, SO 2  or SO 2 NR 2 ; A is oxygen or sulfur;    B is oxygen, sulfur, NR 2  or a bond;    R 1  is hydrogen, halogen, hydroxy, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, cycloalkyloxy, alkenyloxy, alkynyloxy, aryl, aryloxy, arylalkyl, where the 13 last mentioned radicals for their part may be substituted; unsubstituted or substituted four- to six-membered heterocyclyl; 
           unsubstituted or substituted four- to six-membered heterocyclyl-C 1 -C 4 -alkyl; unsubstituted or substituted five- or six-membered heteroaryl having one to four nitrogen atoms or having one to three nitrogen atoms and one oxygen or one sulfur atom or having one oxygen or sulfur atom; or    unsubstituted or substituted five- or six-membered heteroaryl-C 1 -C 4 -alkyl having one to four nitrogen atoms or having one to three nitrogen atoms and one oxygen or one sulfur atom or having one oxygen or sulfur atom;    
           R 2  is hydrogen,-alkyl, alkenyl, alkynyl, cycloalkyl, where the four last mentioned radicals may be partially or fully halogenated; or    R 1  and R 2  together with the nitrogen atom to which they are attached form an unsubstituted or substituted three- to seven-membered heterocycle; 
           Q is a radical from the group consisting of Q 1  to Q 39 ; to processes and intermediates for their preparation and to the use of these compounds or of the compositions comprising these compounds for controlling unwanted plants and for the desiccation/defoliation of plants.

The present invention relates to benzenesulfonamide derivatives of theformula I

in which the variables are as defined below:

-   -   X¹ is hydrogen or halogen;    -   X² is hydrogen, cyano, CS—NH₂, halogen, C₁-C₆-alkyl or        C₁-C₆-haloalkyl;    -   X³ is hydrogen, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₄-alkyl,        C₃-C₇cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl or        phenyl-C₁-C₄-alkyl, where the phenyl radical for its part may be        partially or fully halogenated and/or substituted by one to        three radicals from the group consisting of C₁-C₆-alkyl and        C₁-C₆-alkoxy;    -   Y is a group —C(A)B, SO₂ or SO₂NR²;    -   A is oxygen or sulfur;    -   B is oxygen, sulfur, NR² or a bond;    -   R¹ is hydrogen, halogen, hydroxyl, C₁-C₈-alkyl, C₃-C₇cycloalkyl,        C₃-C₇cyclo-alkyl-C₁-C₄-alkyl, C₂-C₈-alkenyl, C₅-C₇-cycloalkenyl,        C₃-C₈-alkynyl, C₁-C₈-alkoxy, C₃-C₇-cycloalkyloxy,        C₂-C₈-alkenyloxy, C₃-C₈-alkynyloxy, aryl, aryloxy,        aryl-C₁-C₄-alkyl;        -   where the 13 last mentioned radicals for their part may be            partially or fully halogenated and/or may be substituted by            one to three substituents from the group consisting of            cyano, NO₂, hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl,            C₃-C₇cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,            C₃-C₇cycloalkyloxy, C₂-C₆-alkenyloxy, C₃-C₆-alkynyloxy,            C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, amino,            C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylsulfinyl,            C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,            C₁-C₆-haloalkylsulfonyl, C₁-C₆-alkoxysulfonyl, formyl,            C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl,            C₂-C₆-alkenylcarbonyl, C₃-C₆-alkynylcarbonyl, carboxy,            C₁-C₆-alkoxycarbonyl, C₁-C₆-haloalkoxycarbonyl,            C₂-C₆-alkenyloxycarbonyl, C₃-C₆-alkynyloxycarbonyl,            mercaptocarbonyl, C₁-C₆-alkylthiocarbonyl,            C₁-C₆-haloalkylthiocarbonyl, C₂-C₆-alkenylthiocarbonyl,            C₃-C₆-alkynylthiocarbonyl, aminocarbonyl,            C₁-C₆-alkylaminocarbonyl, di(C₁-C₆-alkylamino)carbonyl,            C₁-C₆-haloalkylaminocarbonyl,            di(C₁-C₆-haloalkylamino)carbonyl,            C₂-C₆-alkenyl-aminocarbonyl, di(C₂-C₆-alkenylamino)carbonyl,            C₃-C₆-alkynylamino-carbonyl, di(C₃-C₆-alkynylamino)carbonyl,            phenyl, phenoxy, phenyl-C₁-C₄-alkyl and phenyl-C₁-C₄-alkoxy;        -   four- to six-membered heterocyclyl which may be partially or            fully halogenated and/or substituted by one to three            radicals from the group consisting of C₁-C₆-alkyl and            C₁-C₆-alkoxy; or        -   four- to six-membered heterocyclyl-C₁-C₄-alkyl which may be            partially or fully halogenated and/or substituted by one to            three radicals from the group consisting of C₁-C₆-alkyl and            C₁-C₆-alkoxy; or        -   five- or six-membered heteroaryl having one to four nitrogen            atoms or having one to three nitrogen atoms and one oxygen            or one sulfur atom or having one oxygen or sulfur atom,            which radical may be partially or fully halogenated and/or            substituted by one to three radicals from the group            consisting of C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,            C₁-C₆-haloalkoxy, amino, C₁-C₆-alkylamino and            di(C₁-C₆-alkyl)amino; or        -   five- or six-membered heteroaryl-C₁-C₄-alkyl having one to            four nitrogen atoms or having one to three nitrogen atoms            and one oxygen or one sulfur atom or having one oxygen or            sulfur atom, which radical may be partially or fully            halogenated and/or substituted by one to three radicals from            the group consisting of C₁-C₆-alkyl, C₁-C₆-haloalkyl,            C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, amino, C₁-C₆-alkylamino and            di(C₁-C₆-alkyl)amino;    -   R² is hydrogen, C₁-C₈-alkyl, C₂-C₈-alkenyl, C₃-C₈-alkynyl,        C₃-C₇cycloalkyl, where the four last mentioned radicals may be        partially or fully halogenated; or    -   R¹ and R² together with the nitrogen atom to which they are        attached form a three- to seven-membered heterocycle which for        its part may be partially or fully halogenated and/or        substituted by one to three radicals from the group consisting        of C₁-C₆-alkyl, C₁-C₆-haloalkyl and C₁-C₆-alkoxy;    -   Q is a radical from the group consisting of Q¹ to Q³⁹    -   A¹ to A¹⁷ are oxygen or sulfur;    -   R³, R⁴, R⁷, R⁸, R¹¹, R¹², R¹⁸, R¹⁹, R²⁷, R²⁹, R³², R³³, R³⁸,        R³⁹, R⁴⁴, R⁴⁵, R⁴⁶ and R⁴⁷ are hydrogen, cyano, hydroxyl,        C₁-C₆-alkyl, C₁-C₆-cyanoalkyl, C₁-C₆-haloalkyl,        C₃-C₇-cycloalkyl, C₃-C₇cycloalkyloxy, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,        C₂-C₆-alkenyloxy, C₃-C₆-alkynyl, C₃-C₆-alkynyloxy,        C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, phenyl-C₁-C₆-alkyl,        amino, C₁-C₆-alkylamino or di(C₁-C₆-alkyl)amino; or    -   R³ and R⁴, R¹¹ and R¹², R¹⁸ and R^(19,) or R⁴⁶ and R⁴⁷ together        with the atoms to which they are attached form a three- to        seven-membered heterocycle which for its part may be partially        or fully halogenated and/or substituted by one to three radicals        from the group consisting of C₁-C₆-alkyl and C₁-C₆-alkoxy;    -   R⁵, R⁶, R⁹, R¹⁰, R¹⁵, R¹⁶, R²⁰, R²¹, R³⁰, R³¹, R³⁵, R³⁶, R⁴¹,        R⁴² and R⁴³ are hydrogen, hydroxyl, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₃-C₇cycloalkyl, C₃-C₇-cycloalkyloxy,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkenyloxy, C₃-C₆-alkynyl,        C₃-C₆-alkynyloxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,        C₁-C₆-alkylsulfonyl, C₁-C₆-alkoxysulfonyl,        C₁-C₆-alkylsulfonyloxy, amino, C₁-C₆-alkylamino or        di(C₁-C₆-alkyl)amino; or    -   R⁵ and R⁶, R⁹ and R¹⁰, R¹⁵ and R¹⁶, R²⁰ and R²¹, or R³⁰ and R³¹        together with the atoms to which they are attached form a three-        to seven-membered heterocycle which for its part may be        partially or fully halogenated and/or substituted by one to        three radicals from the group consisting of C₁-C₆-alkyl and        C₁-C₆-alkoxy;    -   R¹³, R¹⁴, R²², R²³ R²⁵ and R²⁶ are hydrogen, halogen or        C₁-C₆-alkyl;    -   R¹⁷, R²⁸, R³⁴, R³⁷ and R⁴⁰ are hydrogen, halogen, hydroxyl,        C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₇-cycloalkyl,        C₃-C₇-cycloalkyloxy, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₂-C₆-alkenyl,        C₂-C₆-haloalkenyl, C₂-C₆-alkenyloxy, C₃-C₆-alkynyl or        C₃-C₆-alkynyloxy;    -   R²⁴ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,        C₃-C₆-alkynyl, C₁-C₆-haloalkoxy, amino, C₁-C₆-alkylamino or        di(C₁-C₆-alkyl)amino;        and their agriculturally useful salts.

Moreover, the invention relates to processes and intermediates forpreparing compounds of formula I, to compositions comprising them and tothe use of these derivatives or of the compositions comprising them forcontrolling unwanted plants.

Furthermore, the invention relates to the use of the compounds of theformula I or of compositions comprising them for the desiccation and/ordefoliation of plants.

Further, the invention relates to the preparation of herbicidalcompositions and compositions for the desiccation/defoliation of plantsusing the compounds I, and to methods for controlling unwantedvegetation or for the desiccation/defoliation of plants using thecompounds I.

Substituted phenyluracils are disclosed in the literature, for examplein WO 96/07323, WO 96/08151, WO 97/42176 and DE 44 37 197.Phenylpyrazoles are described in WO 95/32188. Bicyclic triazolones aredescribed in WO 02/38562. Furthermore, phenyl-substitutedpyrimidin(ethi)ones (WO 96/07647), phenylpyridazones (WO 99/52878) andtriazole derivatives (WO 96/18618) are known from the literature. WO93/03019 discloses phenyl-substituted sulfonamides.

However, the herbicidal or desiccant/defoliant properties of theprior-art compounds and/or their compatibilities with crop plants arenot always entirely satisfactory. Accordingly, it was an object of thepresent invention to provide novel, in particular herbicidally active,compounds having improved properties.

The object also extends to providing novel compounds withdesiccant/defoliant action.

We have found that this object is achieved by the benzenesulfonamidederivatives of the formula I and their herbicidal action.

Furthermore, we have found herbicidal compositions which comprise thecompounds I and have very good herbicidal action. Moreover, we havefound processes for preparing these compositions and methods forcontrolling unwanted vegetation using the compounds I.

Furthermore, it has been found that the compounds I are also suitablefor desiccating and defoliating plant parts, suitable plants being cropplants, such as cotton, potatoes, oilseed rape, sunflowers, soybeans orbroad beans, in particular cotton. In this respect, the inventionprovides compositions for the desiccation and/or defoliation of plants,processes for preparing these compositions and methods for thedesiccation and/or defoliation of plants using the compounds I.

Depending on the substitution pattern, the compounds of the formula Imay comprise one or more centers of chirality, in which case they arepresent as enantiomers or mixtures of diastereomers. The inventionprovides both the pure enantiomers or diastereomers and their mixtures.

The compounds of the formula I can also be present in the form of theiragriculturally useful salts, the type of salt generally beingimmaterial. Suitable salts are, in general, the salts of those cationsor the acid addition salts of those acids whose cations and anions,respectively, have no adverse effect on the herbicidal action of thecompounds I.

Suitable cations are in particular ions of the alkali metals, preferablylithium, sodium and potassium, of the alkaline earth metals, preferablycalcium and magnesium, and of the transition metals, preferablymanganese, copper, zinc and iron, and also ammonium, where, if desired,one to four hydrogen atoms may be replaced by C₁-C₄-alkyl,hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium,dimethylammonium, diisopropylammonium, tetramethylammonium,tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-yl-ammonium,di-(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermorephosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium,and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogensulfate, sulfate, dihydrogenphosphate,hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate,hexafluorophosphate, benzoate and the anions of C₁-C₄-alkanoic acids,preferably formate, acetate, propionate and butyrate.

The organic moieties mentioned for the substituents X², X³, R¹—R⁴⁷ or asradicals on phenyl, heterocyclyl or heteroaryl radicals are collectiveterms for individual enumerations of the individual group members. Allhydrocarbon chains, i.e. all alkyl, alkylene, haloalkyl, cyanoalkyl,phenylalkyl, alkenyl, haloalkenyl, alkynyl, alkoxy, alkylenoxy,haloalkoxy, alkylamino, dialkylamino and alkoxyalkyl moieties can bestraight-chain or branched. Unless indicated otherwise, halogenatedsubstituents preferably carry one to five identical or different halogenatoms. The term “halogen” denotes in each case fluorine, chlorine,bromine or iodine.

Examples of Other Meanings are:

-   -   C₁-C₄-alkyl and the alkyl moieties of        C₁-C₆-alkoxycarbonyl-C₁-C₄-alkyl,        C₂-C₆-alkynyloxycarbonyl-C₁-C₄-alkyl, aryl-C₁-C₄-alkyl,        cycloalkyl-C₁-C₄-alkyl, heterocyclyl-C₁-C₄-alkyl and        heteroaryl-C₁-C₄-alkyl: methyl, ethyl, n-propyl, 1-methylethyl,        n-butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;    -   C₁-C₆-alkyl and the C₁-C₆-alkyl moieties of C₁-C₆-cyanoalkyl,        C₁-C₆-alkylthio, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino,        C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylcarbonyl,        C₁-C₆-alkylthiocarbonyl, C₁-C₆-alkylaminocarbonyl,        di(C₁-C₆-alkyl)aminocarbonyl: C₁-C₄-alkyl as mentioned above,        and also, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl,        3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl,        1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl,        2-methylpentyl, 3-methylpentyl, 4methylpentyl,        1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,        2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl,        1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,        1-ethyl-1-methylpropyl and 1-ethyl-3-methylpropyl;    -   C₁-C₈-alkyl: C₁-C₆-alkyl as mentioned above, and also, for        example, heptyl, 2-methylhexyl, 3-methylhexyl,        2,2-dimethylpentyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl,        3,3-dimethylpentyl, 2,2-dimethyl-3-methylbutyl, octyl,        2-methylheptyl, 3-methylheptyl, 4-methylheptyl,        2,2-dimethylhexyl, 2,3-dimethylhexyl, 2,4-dimethylhexyl,        3,3-dimethylhexyl, 2,2,3-trimethylpentyl, 2,3,3-trimethylpentyl,        2,3,4-trimethylpentyl and 2,2,3,3-tetramethylbutyl;    -   C₃-C₇-cycloalkyl and the C₃-C₇-cycloalkyl moieties of        C₃-C₇-cycloalkyl-C₁-C₄-alkyl and C₃-C₇-cycloalkyloxy: a        monocyclic saturated hydrocarbon having 3 to 7 ring members,        such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and        cycloheptyl;    -   C₅-C₇-cycloalkenyl: a monocyclic unsaturated hydrocarbon having        5 to 7 ring members, for example 1-cyclopentenyl,        2-cyclopentenyl, 3-cyclopentenyl, 2,4-cyclopentadienyl,        1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl,        1,3-cyclohexadienyl, 2,5-cyclohexadienyl, 1-cycloheptenyl,        2-cycloheptenyl, 3-cycloheptenyl, 4-cycloheptenyl,        2,6cycloheptadienyl, 3,5-cycloheptadienyl;    -   four- to six-membered heterocyclyl: a monocyclic saturated or        partially unsaturated hydrocarbon having four to six ring        members as mentioned above which, in addition to carbon atoms,        may comprise one to four nitrogen atoms, one or two oxygen        atoms, one sulfur atom, one to three nitrogen atoms and one        oxygen or one sulfur atom or one oxygen and one sulfur atom and        which may be attached via a carbon atom or a nitrogen atom,        -   for example 2-oxetanyl, 3-oxetanyl, 3-thiethanyl,            1-azetidinyl, 2-azetidinyl, 1-azetinyl, 2-azetinyl;        -   for example 2-tetrahydrofuranyl, 3-tetrahydrofuranyl,            2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl,            3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl,            5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl,            5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl,            5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl,            5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl,            5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl,            1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,            1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,            1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl,            1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl,            1,2,3,4-tetrazolidin-5-yl;        -   for example 1 -pyrrolidinyl, 2-isothiazolidinyl,            2-isothiazolidinyl, 1 -pyrazolidinyl, 3-oxazolidinyl,            3-thiazolidinyl, 1-imidazolidinyl, 1,2,4-triazolidin-1-yl,            1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,            1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,            1,2,3,4-tetrazolidin-5-yl;        -   for example 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl,            2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl,            2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl,            2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl,            4,5-dihydropyrrol-2-yl, 4,5-dihydropyrrol-3-yl,            2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl,            4,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-3-yl,            2,3-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl,            2,5-dihydroisoxazol-4-yl, 2,3-dihydroisoxazolyl,            4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-5-yl,            2,3-dihydroisoxazol-5-yl, 4,5-dihydroisothiazol-3-yl,            2,5-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-3-yl,            4,5-dihydroisothiazol-4yl, 2,5-dihydroisothiazol-4-yl,            2,3-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl,            2,5-dihydroisothiazol-5-yl, 2,3-dihydroisothiazol-5-yl,            2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl,            2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl,            3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl,            3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-3-yl,            4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl,            2,3-dihydroimidazol-2-yl, 2,3-dihydroimidazol-3-yl,            2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl,            4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl,            4,5-dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl,            2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl,            2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl,            2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-3-yl,            3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl,            2,3-dihydrothiazol-3-yl, 2,3-dihydrothiazolyl,            2,3-dihydrothiazol-5-yl, 3,4-dihydrothiazol-3-yl,            3,4-dihydrothiazolyl, 3,4-dihydrothiazo!-5-yl,            3,4-dihydrothiazol-2-yl, 3,4-dihydrothiazol-3-yl,            3,4-dihydrothiazolyl;        -   for example 4,5-dihydropyrrol-1-yl, 2,5-dihydropyrrol-1-yl,            4,5-dihydroisoxazol-2-yl, 2,3-dihydroisoxazol-1-yl,            4,5-dihydroisothiazol-1-yl, 2,3-dihydroisothiazol-1-yl,            2,3-dihydropyrazol-1-yl, 4,5-dihydropyrazol-1-yl,            3,4-dihydropyrazol-1-yl, 2,3-dihydroimidazol-1-yl,            4,5-dihydroimidazol-1-yl, 2,5-dihydroimidazol-1-yl,            2,3-dihydrooxazol-2-yl, 3,4-dihydrooxazol-2-yl,            2,3-dihydrothiazol-2-yl, 3,4-dihydrothiazol-2-yl;        -   for example 2-piperidinyl, 3-piperidinyl, 4-piperidinyl,            1,3-dioxan-5-yl, 1,3-dithian-5-yl, 2-tetrahydropyranyl,            4-tetrahydropyranyl, 2-tetrahydrothiopyranyl,            4-tetrahydrothiopyranyl, 3-hexahydropyridazinyl,            4-hexahydropyridazinyl, 2-hexahydropyrimidinyl,            4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl,            2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl,            1,2,4-hexahydrotriazin-3-yl, tetrahydro-1,3-oxazin-2-yl,            tetrahydro-1,3-oxazin-6-yl, 2-morpholinyl, 3-morpholinyl;        -   for example 1-piperidinyl, 1-hexahydropyridazinyl,            1-hexahydropyrimidinyl, 1-piperazinyl,            1,3,5-hexahydrotriazin-1-yl, 1,2,4-hexahydrotriazin-1-yl,            tetrahydro-1,3-oxazin-1-yl, 1-morpholinyl;        -   for example 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl,            2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl,            2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopyran-5-yl,            2H-thiopyran-6-yl, 5,6-dihydro-4H-1,3-oxazin-2-yl;    -   three- to seven-membered heterocyclyl: four- to six-membered        heterocyclyl as mentioned above, and also        -   for example 2-oxiranyl, 1-aziridinyl, 2-aziridinyl,            2-thiiranyl;        -   for example azepan-2-yl, azepan-3-yl, azepan-4-yl,            oxepan-2-yl, oxepan-3-yl, oxepan-4-yl, thiepan-2-yl,            thiepan-3-yl, thiepan-4-yl, 1,2-diazepan-3-yl,            1,2-diazepan-4-yl, 1,2-diazepan-5-yl;        -   for example azepan-1-yl, 1,2-diazepan-1-yl,            1,4-oxazepan-4-yl, 1,4-thiazepan-4-yl;        -   for example 2,3,6,7-tetrahydro-1H-azepin-2-yl,            2,3,6,7-tetrahydro-1H-azepin-3-yl,            2,3,6,7-tetrahydro-1H-azepin-4-yl,            2,3,4,5-tetrahydro-1H-azepin-2-yl,            2,3,4,5-tetrahydro-1H-azepin-3-yl,            2,3,4,5-tetrahydro-1H-azepin-4-yl, 1H-azepin-2-yl,            1H-azepin-3-yl, 1H-azepin-4-yl, oxepin-2-yl, oxepin-3-yl,            oxepin4-yl, thiepin-2-yl, thiepin-3-yl, thiepin-4yl,            1,4-oxazepin-2-yl, 1,4-oxazepin-3-yl, 1,4-oxazepin-5-yl,            1,4-oxazepin-6-yl, 1,4-oxazepin-7-yl, 1,4-thiazepin-2-yl,            1,4-thiazepin-3-yl, 1,4-thiazepin-5-yl, 1,4-thiazepin-6-yl,            1,4-thiazepin-7-yl,            4,5,6,7-tetrahydro-1H-[1,3]-diazepin-2-yl,            4,5,6,7-tetrahydro-1H-[1,3]-diazepin-4-yl,            4,5,6,7-tetrahydro-1H-[1,3]-diazepin-5-yl,            4,5,6,7-tetrahydro-1H-[1,3]-diazepin-6-yl,            4,5,6,7-tetrahydro-1H-[1,3]-diazepin-7-yl,            2,3,4,5-tetrahydro-1H-[1,4]-diazepin-2-yl,            2,3,4,5-tetrahydro-1H-[1,4]-diazepin-3-yl,            2,3,4,5-tetrahydro-1H-[1,4]-diazepin-5-yl,            2,3,4,5-tetrahydro-1H-[1,4]-diazepin-6-yl,            2,3,4,5-tetrahydro-1H-[1,4]-diazepin-7-yl,            2,3-dihydro-1H-[1,2]diazepin-3-yl,            2,3-dihydro-1H-[1,2]diazepin-4-yl,            2,3-dihydro-1H-[1,2]diazepin-5-yl,            2,3-dihydro-1H-[1,2]diazepin-6-yl,            2,3-dihydro-1H-[1,2]diazepin-7-yl,            4,7-dihydro-[1,4]-oxazepin-2-yl,            4,7-dihydro-[1,4]-oxazepin-3-yl,            4,7-dihydro-[1,4]-oxazepin-5-yl,            4,7-dihydro-[1,4]-oxazepin-6-yl,            4,7-dihydro-[1,4]-oxazepin-7-yl,            2,3-dihydro-[1,3]-thiazepin-2-yl,            2,3-dihydro-[1,3]-thiazepin-4-yl,            2,3-dihydro-[1,3]-thiazepin-5-yl,            2,3-dihydro-[1,3]-thiazepin-6-yl,            2,3-dihydro-[1,3]-thiazepin-7-yl;        -   for example azepin-1-yl, 2,3,6,7-tetrahydroazepin-1-yl,            2,3,4,5-tetrahydroazepin-1-yl,            4,5,6,7-tetrahydro-[1,3]-diazepin-1-yl,            2,3,4,5-tetrahydro-[1,4]-diazepin-1-yl,            2,3-dihydro-[1,2]diazepin-1-yl,            4,7-dihydro-[1,4]-oxazepin-4-yl,            2,3-dihydro-[1,3]-thiazepin-3-yl;    -   C₂-C₄-alkenyl and the alkenyl moieties of        C₁-C₆-alkoxycarbonyl-C₂-C₄-alkenyl: ethenyl, 1-propenyl,        2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl,        1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,        2-methyl-2-propenyl;    -   C₃-C₆-alkenyl: for example 1-propenyl, 2-propenyl,        1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl,        1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,        2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl,        4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl,        3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl,        3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl,        3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl,        1,2-dimethyl-1-propenyl, 1,2-di-methyl-2-propenyl,        1-ethyl-1l-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl,        3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl,        2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl,        1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl,        4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl,        3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl,        2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl,        1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,        1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl,        1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl,        1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,        2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl,        2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl,        3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,        1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,        2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,        1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,        1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;    -   C₂₋C₆-alkenyl and the C₂₋C₆-alkenyl moieties of        C₂-C₆-alkenyloxy, C₂-C₆-alkenylcarbonyl,        C₂-C₆-alkenyloxycarbonyl, C₂-C₆-alkenyloxycarbonyl-C₁-C₄-alkyl,        C₂-C₆-alkenylthiocarbonyl, C₂-C₆-alkenylaminocarbonyl,        di(C₂-C₆-alkenyl)aminocarbonyl: C₃-C₆-alkenyl as mentioned        above, and also ethenyl;    -   C₂-C₈-alkenyl and the C₂-C₈-alkenyl moieties of        C₂-C₈-alkenyloxy: C₂-C₆-alkenyl as mentioned above, and also,        for example, 1-heptenyl, 2-heptenyl, 3-heptenyl,        2-methyl-1-hexenyl, 2-methyl-2-hexenyl, 2-methyl-3-hexenyl,        2-methyl-4-hexenyl, 2-methyl-5-hexenyl, 3-methyl-1-hexenyl,        3-methyl-2-hexenyl, 3-methyl-3-hexenyl, 3-methyl-4-hexenyl,        3-methyl-5-hexenyl, 2,2-dimethyl-3-pentenyl, 2,2-dimethyl-4        -pentenyl, 2,3-dimethyl-1-pentenyl, 2,3-dimethyl-2-pentenyl,        2,3-dimethyl-3-pentenyl, 2,3-dimethyl-4-pentenyl,        2,4-dimethyl-1-pentenyl, 2,4-dimethyl-2-pentenyl,        3,3-dimethyl-1-pentenyl, 2,2-dimethyl-3-methyl-3-butentyl,        1-octenyl, 2-octenyl, 3-octenyl, 4-octenyl, 2-methyl-1-heptenyl,        2-methyl-2-heptenyl, 2-methyl-3-heptenyl, 2-methyl-4-heptenyl,        2-methyl-5-heptenyl, 2-methyl-6-heptenyl, 3-methyl-1-heptenyl,        3-methyl-2-heptenyl, 3-methyl-3-heptenyl, 3-methyl-4-heptenyl,        3-methyl-5-heptenyl, 3-methyl-6-heptenyl, 4-methyl-1-heptenyl,        4-methyl-2-heptenyl, 4-methyl-3-heptenyl,        2,2-dimethyl-3-hexenyl, 2,2-dimethyl-4-hexenyl,        2,2-dimethyl-5-hexenyl, 2,3-dimethyl-1-hexenyl,        2,3-dimethyl-2-hexenyl, 2,3-dimethyl-3-hexenyl,        2,3-dimethyl-4-hexenyl, 2,3-dimethyl-5-hexenyl,        2,4-dimethyl-1-hexenyl, 2,4-dimethyl-2-hexenyl,        2,4-dimethyl-3-hexenyl, 2,4-dimethyl-4-hexenyl,        2,4-dimethyl-5-hexenyl, 3,3-dimethyl-1-hexenyl,        3,3-dimethyl-4-hexenyl, 3,3-dimethyl-5-hexenyl,        2,2,3-trimethyl-3-pentenyl, 2,2,3-trimethyl-4-pentenyl,        2,3,3-trimethyl-1-pentenyl, 2,3,3-trimethyl-4-pentenyl,        2,3,4trimethyl-1-pentenyl and 2,3,4-trimethyl-2-pentenyl;    -   C₃-C₆-alkynyl and the C₃-C₆-alkynyl moieties of        C₃-C₆-alkynyloxy, C₃-C₆-alkynyl-carbonyl,        C₃-C₆-alkynyloxycarbonyl, C₃-C₆-alkynylthiocarbonyl,        C₃-C₆-alkynyl-aminocarbonyl, di(C₃-C₆-alkynyl)aminocarbonyl: for        example 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl,        1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl,        4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl,        2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl,        1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl,        5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl,        1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl,        3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl,        4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl,        1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl,        2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl,        1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and        1-ethyl-1-methyl-2-propynyl;    -   C₃-C₈-alkynyl and the C₃-C₈-alkynyl moieties of        C₃-C₈-alkynyloxy: C₃-C₆-alkynyl as mentioned above, and also,        for example, 1-heptynyl, 2-heptynyl, 3-heptynyl,        2-methyl-3-hexynyl, 2-methyl-4-hexynyl, 2-methyl-5-hexynyl,        3-methyl-1-hexynyl, 3-methyl-4-hexynyl, 3-methyl-5-hexynyl,        2,2-dimethyl-3-pentynyl, 2,2-dimethyl-4-pentynyl,        2,3-dimethyl-4pentynyl, 3,3-dimethyl-1-pentynyl, 1-octynyl,        2-octynyl, 3-octynyl, 4-octynyl, 2-methyl-3-heptynyl,        2-methyl-4-heptynyl, 2-methyl-5-heptynyl, 2-methyl-6-heptynyl,        3-methyl-1-heptynyl, 3-methyl-4-heptynyl, 3-methyl-5-heptynyl,        3-methyl-6-heptynyl, 4-methyl-1-heptynyl, 4methyl-2-heptynyl,        2,2-dimethyl-3-hexynyl, 2,2-dimethyl-4-hexynyl,        2,2-dimethyl-5-hexynyl, 2,3-dimethyl-4-hexynyl,        2,3-dimethyl-5-hexynyl, 2,4-dimethyl-5-hexynyl,        3,3-dimethyl-1-hexynyl, 3,3-dimethyl-4-hexynyl,        3,3-dimethyl-5-hexynyl, 2,2,3-trimethyl-3-pentynyl,        2,2,3-trimethyl-4-pentynyl and 2,3,3-trimethyl-4-pentynyl;    -   C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which        is partially or fully substituted by fluorine, chlorine, bromine        and/or iodine, i.e., for example, chloromethyl, dichloromethyl,        trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,        chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,        2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl,        2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,        2-chloro-2,2,difluoroethyl, 2,2-dichloro-2-fluoroethyl,        2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl,        3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,        2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl,        2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,        3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl,        heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl,        1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl,        4-fluorobutyl, 4chlorobutyl, 4-bromobutyl and nonafluorobutyl;    -   C₁-C₆-haloalkyl and the C₁-C₆-haloalkyl moieties of        C₁-C₆-haloalkylthio, C₁-C₆-haloalkylsulfinyl,        C₁-C₆-haloalkylsulfonyl, C₁-C₆-haloalkylcarbonyl,        C₁-C₆-haloalkylthiocarbonyl, C₁-C₆-haloalkylaminocarbonyl,        di(C₁-C₆-haloalkyl)aminocarbonyl: C₁-C₄-haloalkyl as mentioned        above, and also, for example, 5-fluoropentyl, 5-chloropentyl,        5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl,        6-chlorohexyl, 6-bromohexyl, 6-iodohexyl and dodecafluorohexyl;    -   C₁-C₈-haloalkyl: C₁-C₆-haloalkyl as mentioned above, and also,        for example, 7-fluoroheptyl, 7-chloroheptyl, 7-bromoheptyl,        7-iodoheptyl, perfluoroheptyl, 8-fluorooctyl, 8-chlorooctyl,        8-bromooctyl, 8-iodooctyl and perfluorooctyl;    -   C₂-C₆-haloalkenyl: a C₂-C₆-alkenyl radical as mentioned above        which is partially or fully substituted by fluorine, chlorine,        bromine and/or iodine, for example 2-chlorovinyl, 2-chloroallyl,        3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl,        2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromovinyl,        2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl,        2,3,3-tribromoallyl and 2,3-dibromobut-2-enyl;    -   C₂-C₈-haloalkenyl: a C₂-C₆-haloalkenyl radical as mentioned        above, and also, for example, 2-chloro-1-heptenyl,        3-chloro-1-heptenyl, 2,3-dichloro-1-heptenyl,        3,3-dichloro-1-heptenyl, 2,3,3-trichloro-1-heptenyl,        2-bromo-1-heptenyl, 3-bromo-1-heptenyl, 2,3-dibromo-1-heptenyl,        3,3-dibromo-1-heptenyl, 2,3,3-tribromo-1-heptenyl,        2-chloro-1-octenyl, 3-chloro-1-octenyl, 2,3-dichloro-1-octenyl,        3,3-dichloro-1-octenyl, 2,3,3-trichloro-1-octenyl,        2-bromo-1-octenyl, 3-bromo-1-octenyl, 2,3-dibromo-1-octenyl,        3,3-dibromo-1-octenyl and 2,3,3-tribromo-1-octenyl;    -   C₃-C₆-haloalkynyl: a C₃-C₆-alkynyl radical as mentioned above        which is partially or fully substituted by fluorine, chlorine,        bromine and/or iodine, for example 1,1-difluoroprop-2-yn-1-yl,        3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl,        4chlorobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl,        4iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl,        5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl and        6-iodohex-5-yn-1-yl;    -   C₁-C₄-alkoxy and the C₁-C₄-alkoxy moieties of        C₁-C₄-alkoxy-C₁-C₄-alkyl and phenyl-C₁-C₄-alkoxy: for example        methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy,        1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;    -   C₁-C₆-alkoxy and the C₁-C₆-alkoxy moieties of        C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxycarbonyl,        C₁-C₆-alkoxycarbonyl-C₁-C₄-alkyl,        C₁-C₆-alkoxycarbonyl-C₂-C₄-alkenyl, C₁-C₆-alkoxysulfonyl:        C₁-C₄-alkoxy as mentioned above, and also, for example, pentoxy,        1-methylbutoxy, 2-methylbutoxy, 3-methoxylbutoxy,        1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy,        1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy,        3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy,        1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy,        2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy,        2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy,        1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy;    -   C₁-C₈-alkoxy: C₁-C₆-alkoxy as mentioned above, and also, for        example, heptoxy, 2-methylhexoxy, 3-methylhexoxy,        2,2-dimethylpentoxy, 2,3-dimethylpentoxy, 2,4-dimethylpentoxy,        3,3-dimethylpentoxy, 2,2-dimethyl-3-methylbutoxy, octoxy,        2-methylheptoxy, 3-methylheptoxy, 4-methylheptoxy,        2,2-dimethylhexoxy, 2,3-dimethylhexoxy, 2,4-dimethylhexoxy,        3,3-dimethylhexoxy, 2,2,3-trimethylpentoxy,        2,3,3-trimethylpentoxy, 2,3,4trimethylpentoxy and        2,2,3,3-tetramethylbutoxy;    -   C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above        which is partially or fully substituted by fluorine, chlorine,        bromine and/or iodine, i.e., for example, fluoromethoxy,        difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy,        bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy,        2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,        2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,        2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,        2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy,        3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy,        2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy,        2,3-difluoropropoxy, 2,3-dichloropropoxy,        3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,        2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy,        1-(fluoromethyl)-2-fluoroethoxy,        1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy,        4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and        nonafluorobutoxy;    -   C₁-C₆-haloalkoxy and the C₁-C₆-haloalkoxy moieties of        C₁-C₆-haloalkoxycarbonyl: C₁-C₄-haloalkoxy as mentioned above,        and also, for example, 5-fluoropentoxy, 5-chloropentoxy,        5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy,        6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy and        dodecafluorohexoxy;    -   C₁-C₆-alkoxy-C₁-C₄-alkyl and the alkyl radicals of        C₁-C₆-alkylthio-C₁-C₄-alkyl: a C₁-C₄-alkyl which is substituted        by C₁-C₆-alkoxy as mentioned above, i.e., for example,        methoxymethyl, ethoxymethyl, propoxymethyl,        (1-methylethoxy)methyl, butoxymethyl, (1-methylpropoxy)methyl,        (2-methylpropoxy)methyl, (1,1-dimethylethoxy)methyl,        2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(propoxy)ethyl,        2-(1-methylethoxy)ethyl, 2-(butoxy)ethyl,        2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl,        2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl,        2-(ethoxy)propyl, 2-(propoxy)propyl, 2-(1-methylethoxy)propyl,        2-(butoxy)propyl, 2-(1-methylpropoxy)propyl,        2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl,        3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(propoxy)propyl,        3-(1-methylethoxy)propyl, 3-(butoxy)propyl,        3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl,        3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl,        2-(propoxy)butyl, 2-(1-methylethoxy)-butyl, 2-(butoxy)butyl,        2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl,        2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl,        3-(propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(butoxy)butyl,        3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl,        3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl,        4-(propoxy)butyl, 4(1l-methylethoxy)butyl, 4-(butoxy)butyl,        4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl and        4-(1,1-dimethylethoxy)butyl;    -   C₁-C₆-alkoxycarbonyl-C₁-C₄-alkyl: C₁-C₄-alkyl which is        substituted by C₁-C₆-alkoxycarbonyl as mentioned above, i.e.,        for example, methoxycarbonylmethyl, ethoxycarbonylmethyl,        propoxycarbonylmethyl, (1-methylethoxycarbonyl)methyl,        butoxycarbonylmethyl, (1-methylpropoxycarbonyl)methyl,        (2-methylpropoxycarbonyl)methyl,        (1,1-dimethylethoxycarbonyl)methyl, 2-(methoxycarbonyl)ethyl,        2-(ethoxycarbonyl)ethyl, 2-(propoxycarbonyl)ethyl,        2-(1-methylethoxycarbonyl)ethyl, 2-(butoxycarbonyl)ethyl,        2-(1-methylpropoxycarbonyl)ethyl,        2-(2-methylpropoxycarbonyl)ethyl,        2-(1,1-dimethylethoxycarbonyl)ethyl, 2-(methoxycarbonyl)propyl,        2-(ethoxycarbonyl)propyl, 2-(propoxycarbonyl)propyl,        2-(1-methylethoxycarbonyl)propyl, 2-(butoxycarbonyl)propyl,        2-(1-methylpropoxycarbonyl)propyl,        2-(2-methylpropoxycarbonyl)propyl,        2-(1,1-dimethylethoxycarbonyl)propyl, 3-(methoxycarbonyl)propyl,        3-(ethoxycarbonyl)propyl, 3-(propoxycarbonyl)propyl,        3-(1-methylethoxycarbonyl)propyl, 3-(butoxycarbonyl)propyl,        3-(1-methylpropoxycarbonyl)propyl,        3-(2-methylpropoxycarbonyl)propyl,        3-(1,1-dimethylethoxycarbonyl)propyl, 2-(methoxycarbonyl)butyl,        2-(ethoxycarbonyl)butyl, 2-(propoxycarbonyl)butyl,        2-(1-methylethoxycarbonyl)butyl, 2-(butoxycarbonyl)butyl,        2-(1-methylpropoxycarbonyl)butyl,        2-(2-methylpropoxycarbonyl)butyl,        2-(1,1-dimethylethoxycarbonyl)butyl, 3-(methoxycarbonyl)butyl,        3-(ethoxycarbonyl)butyl, 3-(propoxycarbonyl)butyl,        3-(1-methylethoxycarbonyl)butyl, 3-(butoxycarbonyl)butyl,        3-(1-methylpropoxycarbonyl)butyl,        3-(2-methylpropoxycarbonyl)butyl,        3-(1,1-dimethylethoxycarbonyl)butyl, 4-(methoxycarbonyl)butyl,        4-(ethoxycarbonyl)butyl, 4-(propoxycarbonyl)butyl,        4-(1-methylethoxycarbonyl)butyl, 4-(butoxycarbonyl)butyl,        4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy and        4-(1,1-dimethylethoxycarbonyl)butyl;    -   C₁-C₄-alkylthio: for example methylthio, ethylthio,        n-propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio,        2-methylpropylthio and 1,1-dimethylethylthio; p1        C₁-C₆-alkylthio: C₁-C₄-alkylthio as mentioned above, and also,        for example, pentylthio, methylbutylthio, 2-methylbutylthio,        3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio,        hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio,        1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio,        4-methylpentylthio, 1,1-dimethylbutylthio,        1,2-dimethylbutylthio, 1,3-dimethylbutylthio,        2,2-dimethylbutylthio, 2,3-dimethylbutylthio,        3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio,        1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,        1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio;    -   C₁-C₈-alkylthio: C₁-C₆-alkylthio as mentioned above and the        alkylthio moieties of C₁-C₈-alkylthio-C₁-C₈-alkyl, and also, for        example, heptylthio, 2-methylhexylthio, 3-methylhexylthio,        2,2-dimethylpentylthio, 2,3-dimethylpentylthio,        2,4-dimethylpentylthio, 3,3-dimethylpentylthio,        2,2-dimethyl-3-methylbutylthio, octylthio, 2-methylheptylthio,        3-methylheptylthio, 4-methylheptylthio, 2,2-dimethylhexylthio,        2,3-dimethylhexylthio, 2,4-dimethylhexylthio,        3,3-dimethylhexylthio, 2,2,3-trimethylpentylthio,        2,3,3-trimethylpentylthio, 2,3,4-trimethylpentylthio and        2,2,3,3-tetramethylbutylthio;    -   C₁-C₆-alkylamino: for example methylamino, ethylamino,        propylamino, 1-methylethylamino, butylamino,        1-methylpropylamino, 2-methylpropylamino,        1,1-dimethylethylamino, pentylamino, 1-methylbutylamino,        2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino,        1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino,        1,2-dimethylpropylamino, 1-methylpentylamino,        2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino,        1,1-dimethylbutylamino, 1,2-dimethylbutylamino,        1,3-dimethylbutylamino, 2,2-dimethylbutylamino,        2,3-dimethylbutylamino, 3,3-dimethylbutylamino,        1-ethylbutylamino, 2-ethylbutylamino,        1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino,        1-ethyl-1-methylpropylamino and 1-ethyl-2-methylpropylamino;    -   di(C₁-C₄-alkyl)amino: for example N,N-dimethylamino,        N,N-diethylamino, N,N-dipropylamino, N,N-di(1-methylethyl)amino,        N,N-dibutylamino, N,N-di(1-methylpropyl)amino,        N,N-di(2-methylpropyl)amino, N,N-di(1,1-dimethylethyl)amino,        N-ethyl-N-methylamino, N-methyl-N-propylamino,        N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino,        N-methyl-N-(1-methylpropyl)-amino,        N-methyl-N-(2-methylpropyl)amino,        N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino,        N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino,        N-ethyl-N-(1-methylpropyl)amino,        N-ethyl-N-(2-methylpropyl)amino,        N-ethyl-N-(1,1-dimethylethyl)amino,        N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino,        N-(1-methylpropyl)-N-propylamino,        N-(2-methylpropyl)-N-propylamino,        N-(1,1-dimethylethyl)-N-propylamino,        N-butyl-N-(1-methylethyl)amino,        N-(1-methylethyl)-N-(1-methylpropyl)amino,        N-(1-methylethyl)-N-(2-methylpropyl)amino,        N-(1,1-dimethylethyl)-N-(1-methylethyl)amino,        N-butyl-N-(1-methylpropyl)amino,        N-butyl-N-(2-methylpropyl)amino,        N-butyl-N-(1,1-dimethylethyl)amino,        N-(1-methylpropyl)-N-(2-methylpropyl)amino,        N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino and        N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino;    -   di(C₁-C₆-alkyl)amino and the dialkylamino moieties of        di(C₁-C₆-alkyl)amino-C₁-C₆-alkyl, di(C₁-C₆-alkyl)aminocarbonyl        and di(C₁-C₆-alkyl)aminocarbonyl-C₁-C₆-alkyl:        di(C₁-C₄-alkyl)amino as mentioned above, for example,        N,N-dipentylamino, N,N-dihexylamino, N-methyl-N-pentylamino,        N-ethyl-N-pentylamino, N-methyl-N-hexylamino and        N-ethyl-N-hexylamino;    -   aryl and the aryl moieties of aryloxy and aryl-C₁-C₄-alkyl: a        monocyclic to tricyclic aromatic carbocycle having 6 to 14 ring        members, such as, for example, phenyl, naphthyl and anthracenyl;    -   5- or 6-membered heteroaryl and the 5- or 6-membered heteroaryl        moieties of 5- or 6-membered heteroaryl-C₁-C₆-alkyl: aromatic 5-        or 6-membered heterocycles which, in addition to carbon atoms,        may comprise one to four nitrogen atoms or one to three nitrogen        atoms and one sulfur or oxygen atom or one oxygen or sulfur atom        as ring members, for example 2-furyl, 3-furyl, 2-thienyl,        3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl,        5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl,        3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl,        5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl,        4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4oxadiazol-5-yl,        1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,        1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl,        1,3,4-triazol-2-yl and tetrazol-2-yl; 2-pyridinyl, 3-pyridinyl,        4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl,        4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl        and 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl        and 1,2,4,5-tetrazinyl.

In a particular embodiment, the variables of the compounds of theformula I are as defined below, these definitions being, both on theirown and in combination with one another, particular embodiments of thecompounds of the formula I:

Preference is given to the benzenesulfonamides of the formula I in which

-   -   X¹ is hydrogen, fluorine or chlorine;        -   particularly preferably hydrogen or fluorine;        -   especially preferably fluorine.

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   X² is hydrogen, cyano, CS—NH₂ or halogen;        -   particularly preferably hydrogen, cyano or halogen such as            fluorine and chlorine;        -   especially preferably chlorine.

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   X¹ is hydrogen, fluorine or chlorine;        -   particularly preferably hydrogen or fluorine;        -   especially preferably fluorine; and    -   X² is hydrogen, cyano, CS—NH₂ or halogen;        -   particularly preferably hydrogen, cyano, halogen such as            fluorine and chlorine;        -   especially preferably chlorine.

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   X³ is hydrogen, cyano, C₁-C₆-alkyl or phenyl-C₁-C₄-alkyl;        -   particularly preferably hydrogen, cyano, C₁-C₄-alkyl, such            as CH₃, and C₂H₅, or benzyl;        -   especially preferably hydrogen or cyano;        -   with extraordinary preference hydrogen.

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   Y is a group C(A)B;        -   particularly preferably C(A)B, where A is oxygen;        -   especially preferably C(A)B, where A is oxygen and B is            oxygen or sulfur;        -   with extraordinary preference C(A)B, where A and B are            oxygen.

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   Y is a group C(A)B;        -   particularly preferably C(A)B, where A is oxygen;        -   especially preferably C(A)B, where A is oxygen and B is NR².

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   Y is a group C(A)B;        -   particularly preferably C(A)B, where A is oxygen;        -   especially preferably C(A)B, where A is oxygen and B is a            bond.

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   R¹ is hydrogen, hydroxyl, C₁-C₈-alkyl, C₁-C₈-haloalkyl,        C₃-C₇-cycloalkyl, C₃-C₇cycloalkyl-C₁-C₄-alkyl, C₂-C₈-alkenyl,        C₂-C₈-haloalkenyl, C₃-C₈-alkynyl, C₁-C₈-alkoxy,        C₁-C₆-alkoxy-C₁-C₄-alkyl, C_(1-C) ₆-alkoxycarbonyl-C₁-C₄-alkyl,        C₁-C₆-alkoxycarbonyl-C₂-C₄-alkenyl,        C₂-C₆-alkenyloxycarbonyl-C₁-C₄-alkyl,        C₃-C₆-alkynyloxycarbonyl-C₁-C₄-alkyl,        C₁-C₆-alkylthio-C₁-C₄-alkyl, aryl, aryl-C₁-C₄-alkyl;        -   four- to six-membered heterocyclyl which may be partially or            fully halogenated and/or may carry one to three radicals            from the group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;        -   four- to six-membered heterocyclyl-C₁-C₄-alkyl which may be            partially or fully halogenated and/or may carry one to three            radicals from the group consisting of C₁-C₄-alkyl and            C₁-C₄-alkoxy;        -   five- or six-membered heteroaryl having one to four nitrogen            atoms or having one to three nitrogen atoms and one oxygen            or one sulfur atom or having one oxygen or sulfur atom,            which radicals may be partially or fully halogenated and/or            may carry one to three radicals from the group consisting of            C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,            C₁-C₄-haloalkoxy, amino, C₁-C₄-alkylamino and            di(C₁-C₄-alkyl)amino;        -   five- or six-membered heteroaryl-C₁-C₄-alkyl having one to            four nitrogen atoms or having one to three nitrogen atoms            and one oxygen or one sulfur atom or having one oxygen or            sulfur atom, which radicals may be partially or fully            halogenated and/or may carry one to three radicals from the            group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;    -   particularly preferably        -   hydrogen, hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl,            C₃-C₇cycloalkyl, C₂-C₆ alkenyl, C₂-C₆-haloalkenyl,            C₃-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,            C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl,            C₁-C₄-alkoxycarbonyl-C₂-C₄-alkenyl,            C₂-C₄-alkenyloxycarbonyl-C₁-C₄-alkyl,            C₃-C₆-alkynyloxycarbonyl-C₁-C₄-alkyl,            C₁-C₄-alkylthio-C₁-C₄-alkyl, phenyl, benzyl;        -   five- or six-membered heterocyclyl which may be partially or            fully halogenated and/or may carry one to three radicals            from the group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;        -   five- or six-membered heteroaryl having one to four nitrogen            atoms or having one to three nitrogen atoms and one oxygen            or one sulfur atom or having one oxygen or sulfur atom,            which radicals may be partially or fully halogenated and/or            may carry one to three radicals from the group consisting of            C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,            C₁-C₄-haloalkoxy, amino, C₁-C₄-alkylamino and            di(C₁-C₄-alkyl)amino;    -   especially preferably    -   C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₅-C₆-cycloalkyl, C₂-C₆-alkenyl,        C₃-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,        C₁-C₄-alkylthio-C₁-C₄-alkyl, phenyl, benzyl;        -   five- or six-membered heterocyclyl which may be partially or            fully halogenated and/or may carry one to three radicals            from the group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;        -   five- or six-membered heteroaryl having one to four nitrogen            atoms or having one to three nitrogen atoms and one oxygen            or one sulfur atom or having one oxygen or sulfur atom,            where the two last mentioned radicals may be partially or            fully halogenated and/or may carry one to three radicals            from the group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;    -   with extraordinary preference        -   C₁-C₄-alkyl, such as C₃, C₂H₅, CH(CH₃)₂, —CH₂—CH₂—CH₃,            C₁-C₄-haloalkyl, such as CF₃, C₅-C₆-cycloalkyl,            C₂-C₄-alkenyl, C₃-C₄-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,            C₁-C₄-alkylthio-C₁-C₄-alkyl, phenyl, benzyl, five- or            six-membered heterocyclyl or five- or six-membered            heteroaryl having one to four nitrogen atoms, where the two            last mentioned radicals may be partially or fully            halogenated and/or may carry one to three radicals from the            group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy.

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   R² is hydrogen, C₁-C₈-alkyl or C₂-C₈-alkenyl, particularly        preferably hydrogen, C₁-C₆-alkyl or C₂-C₆-alkenyl, especially        preferably hydrogen or C₁-C₄-alkyl, with extraordinary        preference hydrogen, CH₃, C₂H₅ or CH(CH₃)₂, with most        extraordinary preference hydrogen or CH₃.

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   R¹ and R² together with the nitrogen atom to which they are        attached form a three- to seven-membered heterocycle which for        its part may be partially or fully halogenated and/or may carry        one to three radicals from the group consisting of C₁-C₆-alkyl,        C₁-C₆-haloalkyl and C₁-C₆-alkoxy;        -   particularly preferably a three- to seven-membered            heterocycle which for its part may be partially or fully            halogenated and/or may carry one to three radicals from the            group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;        -   especially preferably a five- to seven-membered heterocycle            which for its part may be partially or fully halogenated            and/or may carry one to three radicals from the group            consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;        -   with extraordinary preference a five- or six-membered            heterocycle which for its part may be partially or fully            halogenated and/or may carry one to three radicals from the            group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;        -   with most extraordinary preference a heterocycle from the            group consisting of pyrrolidin-1-yl, 2,3-dihydropyrrol-1-yl,            2,5-dihydropyrrol-1-yl, piperidin-1-yl,            1,2,3,4-tetrahydropyridin-1-yl,            1,2,3,6-tetrahydropyridin-1-yl, piperazin-1-yl,            morpholin-4-yl, which heterocycle may for its part be            partially or fully halogenated and/or may carry one to three            radicals from the group consisting of C₁-C₄-alkyl and            C₁-C₄-alkoxy.

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   Y is C(A)B, where A and B are oxygen; and    -   R¹ has the preferred meanings mentioned above.

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   Y is C(A)B, where A is oxygen and B is NR²; and    -   R² is hydrogen, C₁-C₈-alkyl or C₂-C₈-alkenyl, particularly        preferably hydrogen, C₁-C₆-alkyl or C₂-C₆-alkenyl, especially        preferably hydrogen or C₁-C₄-alkyl, with extraordinary        preference hydrogen, CH₃, C₂H₅ or CH(CH₃)₂; with most        extraordinary preference hydrogen or CH₃;    -   with particular preference    -   Y is C(=A)B, where A is oxygen and B is NR²;    -   R² is hydrogen, C₁-C₈-alkyl or C₂-C₈-alkenyl, particularly        preferably hydrogen, C₁-C₆-alkyl or C₂-C₆-alkenyl, especially        preferably hydrogen or C₁-C₄-alkyl, with extraordinary        preference hydrogen, CH₃, C₂H₅ or CH(CH₃)₂;        -   with most extraordinary preference hydrogen or CH₃; and    -   R¹ has the preferred meanings mentioned above.

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   Y is C(A)B where A is oxygen and B is NR²; and    -   R¹ and R² together with the nitrogen atom to which they are        attached, form a three- to seven-membered heterocycle which for        its part may be partially or fully halogenated and/or may carry        one to three radicals from the group consisting of C₁-C₆-alkyl,        C₁-C₆-haloalkyl and C₁-C₆-alkoxy;        -   particularly preferably a three- to seven-membered            heterocycle which for its part may be partially or fully            halogenated and/or may carry one to three radicals from the            group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;        -   especially preferably a five- to seven-membered heterocycle            which for its part may be partially or fully halogenated            and/or may carry one to three radicals from the group            consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;        -   with extraordinary preference a five- or six-membered            heterocycle which for its part may be partially or fully            halogenated and/or may carry one to three radicals from the            group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy;        -   with most extraordinary preference a heterocycle from the            group consisting of pyrrolidin-1-yl, 2,3-dihydropyrrol-1-yl,            2,5-dihydropyrrol-1-yl, piperidin-1-yl,            1,2,3,4tetrahydropyridin-1-yl,            1,2,3,6tetrahydropyridin-1-yl, piperazin-1-yl,            morpholin-4-yl, which for its part may be partially or fully            halogenated and/or may carry one to three radicals from the            group consisting of C₁-C₄-alkyl and C₁-C₄-alkoxy.

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   Y is C(A)B, where A is oxygen and B is a bond; and    -   R¹ has the preferred meanings mentioned above.

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   Y is a group SO₂;    -   particularly preferably    -   Y is SO₂; and    -   R¹ has the preferred meanings mentioned above.

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   Y is a group SO₂NR²;    -   particularly preferably    -   Y is SO₂NR²; and    -   R² is hydrogen, C₁-C₈-alkyl or C₂-C₈-alkenyl, particularly        preferably hydrogen, C₁-C₆-alkyl or C₂-C₆-alkenyl, especially        preferably hydrogen or C₁-C₄-alkyl, with extraordinary        preference hydrogen, CH₃, C₂H₅ or CH(CH₃)₂;        -   with most extraordinary preference hydrogen or CH₃;    -   especially preferably    -   Y is SO₂NR²;    -   R² is hydrogen, C₁-C₈-alkyl or C₂-C₈-alkenyl, particularly        preferably hydrogen, C₁-C₆-alkyl or C₂-C₆-alkenyl, especially        preferably hydrogen or C₁-C₄-alkyl, with extraordinary        preference hydrogen, CH₃, C₂H₅ or CH(CH₃)₂;        -   with most extraordinary preference hydrogen or CH₃; and    -   R¹ has the preferred meanings mentioned above.

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   Q is Q¹, Q², Q⁵, Q⁷, Q⁸, Q¹⁰, Q¹², Q¹³, Q¹⁷, Q²⁰, Q²¹, Q²², Q²³,        Q²⁴, Q²⁷, Q³¹, Q³⁴, Q³⁸ or Q³⁹;        -   particularly preferably Q¹, Q², Q⁵, Q⁷, Q⁸, Q¹⁰, Q¹², Q¹³,            Q¹⁷, Q²⁰, Q²¹, Q²², Q²⁴, Q²⁷, Q³¹, Q³², Q³⁸ or Q³⁹;        -   especially preferably Q⁵, Q⁷, Q²¹, Q²², Q²⁷, Q³², Q³⁸ or            Q³⁹;        -   with extraordinary preference Q²¹, Q³² or Q³⁸.

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   Q is Q¹, Q², Q³, Q⁴, Q⁶, Q⁷, Q⁸, Q⁹, Q¹⁰, Q¹¹, Q¹², Q¹³, Q¹⁴,        Q¹⁵, Q¹⁶, Q¹⁷, Q¹⁸, Q¹⁹, Q²⁰, Q²¹, Q²², Q²³, Q²⁴, Q²⁵, Q²⁶, Q²⁷,        Q²⁸, Q²⁹, Q³⁰, Q³¹, Q³², Q³³, Q³⁴, Q³⁵, Q³⁶, Q³⁷, Q³⁸ or Q³⁹,        -   particularly preferably Q¹, Q², Q⁷, Q⁸, Q¹⁰, Q¹², Q¹³, Q¹⁷,            Q²⁰, Q²¹, Q²², Q²³, Q²⁴, Q²⁷, Q³¹, Q³², Q³⁴, Q³⁸ or Q³⁹,        -   especially preferably Q¹, Q², Q⁷, Q⁸, Q¹⁰, Q¹², Q¹³, Q¹⁷,            Q²⁰, Q²¹, Q²², Q²⁴, Q²⁷, Q³¹, Q³², Q³⁸ or Q³⁹,        -   with extraordinary preference Q⁷, Q²¹, Q²², Q²⁷, Q³², Q³⁸ or            Q³⁹,        -   with most extraordinary preference Q²¹, Q³² or Q³⁸.

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   Q is Q⁷, Q²¹, Q²², Q²⁷, Q³², Q³⁸ or Q³⁹;    -   particularly preferably        -   Q⁷, where Y is SO₂, SO₂NR² or C(A)B where B=oxygen or NR²;        -   Q²¹, where Y is SO₂, SO₂NR² or C(A)B where B =oxygen, sulfur            or NR²,        -   preferably Y is SO₂NR² or C(A)B where B=oxygen or NR²,        -   more preferably Y is SO₂NR² or C(A)B where B=oxygen or NR²,        -   and X² is hydrogen, cyano or halogen, such as fluorine or            chlorine;        -   Q²²; Q²⁷;        -   Q³², where Y is SO₂, SO₂NR² or C(A)B where B =oxygen, sulfur            or NR²;        -   Q³⁸ or Q³⁹;    -   especially preferably        -   Q²¹, where Y is SO₂, SO₂NR² or C(A)B where B=oxygen, sulfur            or NR²,        -   preferably Y is SO₂NR² or C(A)B where B=oxygen or NR²,        -   more preferably Y is SO₂NR² or C(A)B where B=oxygen or NR²,            and        -   X² is hydrogen, cyano or halogen, such as fluorine or            chlorine;        -   Q³², where Y is SO₂, SO₂NR² or C(A)B where B=oxygen, sulfur            or NR²; or        -   Q³⁸.

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   X¹ is hydrogen, fluorine or chlorine;        -   particularly preferably hydrogen or fluorine;        -   especially preferably fluorine;    -   X² is hydrogen, cyano, CS—NH₂ or halogen;        -   particularly preferably hydrogen, halogen, such as fluorine            or chlorine;        -   especially preferably chlorine; and    -   Q is Q¹, Q², Q⁵, Q⁷, Q⁸, Q¹⁰, Q¹², Q¹³, Q¹⁷, Q²⁰, Q²¹, Q²², Q²³,        Q²⁴, Q²⁷, Q³¹, Q³², Q³⁴, Q³⁸ or Q³⁹,        -   particularly preferably Q¹, Q², Q⁵, Q⁷, Q⁸, Q¹⁰, Q¹², Q¹³,            Q¹⁷, Q²⁰, Q²¹, Q²², Q²⁴, Q²⁷, Q³¹, Q³², Q³⁸ or Q³⁹,        -   especially preferably Q⁵, Q⁷, Q²¹, Q²², Q²⁷, Q³², Q³⁸ or            Q³⁹,        -   with extraordinary preference Q²¹, Q³² or Q³⁸.

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   Q is Q¹ to Q³⁹; and    -   R³, R⁴, R⁷, R⁸, R¹¹, R¹², R¹⁸, R¹⁹, R²⁷, R²⁹ R³², R³³, R³⁸, R³⁹        , R⁴⁴, R⁴⁵, R⁴⁶ and R⁴⁷ are hydrogen, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylsulfonyl or amino;        -   preferably hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,            C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylsulfonyl or            amino;        -   especially-preferably hydrogen, CH₃, C₂H₅, CF₃, CHF₂,            CH₂CF₃, OCH₃, OCHF₂, OCF₂CHF₂, SO₂CH₃ or amino;    -   R⁵, R⁶, R⁹, R¹⁰, R¹⁵, R¹⁶, R²⁰, R²¹, R³⁰, R³¹, R³⁵, R³⁶, R⁴¹,        R⁴² and R⁴³        -   are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,            C₁-C₆-haloalkoxy, C₁-C₆-alkylsulfonyl or amino;        -   preferably hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,            C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylsulfonyl or            amino;        -   especially preferably hydrogen, CH₃, C₂H₅, CF₃, CHF₂, OCH₃,            OCHF₂, SO₂CH₃ or amino;    -   R¹³, R¹⁴, R²², R²³ R²⁵ and R²⁶        -   are hydrogen, halogen or C₁-C₄-alkyl;        -   particularly preferably hydrogen, halogen or CH₃;        -   especially preferably hydrogen, chlorine or bromine;    -   R¹⁷, R²⁸, R³⁴, R³⁷ or R⁴⁰        -   are hydrogen, halogen or C₁-C₄-alkyl;        -   particularly preferably hydrogen, halogen or CH₃;        -   especially preferably hydrogen, chlorine or bromine.

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   Q is Q⁵, Q⁷, Q²¹, Q²², Q²⁷, Q³², Q³⁸ or Q³⁹,        -   particularly preferably Q²¹, Q³² or Q³⁸;    -   A¹, A⁸, A⁹, A¹⁰, A¹¹, A¹² A¹³, A¹⁵, A¹⁶ and A¹⁷ are oxygen;    -   R⁷, R⁸, R²⁹, R³², R³³, R³⁸, R³⁹, R⁴⁴, R⁴⁵, R⁴⁶, R⁴⁷        -   are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,            C₁-C₆-haloalkoxy, C₁-C₆-alkylsulfonyl or amino;        -   preferably hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,            C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylsulfonyl or            amino;        -   especially preferably hydrogen, CH₃, C₂H₅, CF₃, CHF₂,            CH₂CF₃, OCH₃, OCHF₂, OCF₂CHF₂, SO₂CH₃ or amino;    -   R³⁰, R³¹, R³⁵, R³⁶, R⁴¹, R⁴², R⁴³        -   are hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,            C₁-C₆-haloalkoxy, C₁-C₆-alkylsulfonyl or amino;        -   preferably hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,            C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylsulfonyl or            amino;        -   especially preferably hydrogen, CH₃, C₂H₅, CF₃, CHF₂, OCH₃,            OCHF₂, SO₂CH₃ or amino; and    -   R³⁴ R³⁷ R⁴⁰        -   are hydrogen, halogen or C₁-C₄-alkyl;        -   particularly preferably hydrogen, halogen or CH₃;        -   especially preferably hydrogen, chlorine or bromine.

Preference is also given to the benzenesulfonamide derivatives of theformula I in which

-   -   Q is Q¹, Q⁷, Q⁸, Q¹⁰, Q¹², Q¹³, Q²¹, Q²³, Q²⁴, Q³¹ or Q³⁴;    -   A¹, A², A³, A⁴, A⁵, A⁶, A⁷, A⁸, A⁹, A¹⁴, A¹⁶ and A¹⁷ are oxygen;        and    -   R³ and R⁴, R⁵ and R⁶, R⁹ and R¹⁰, R¹⁵ and R¹⁶, R¹⁸ and R¹⁹, R²⁰        and R²¹, R³⁰ and R³¹ or R⁴⁶ and R⁴⁷ together with the atoms to        which they are attached form a three- to seven-membered        heterocycle which for its part may be partially or fully        halogenated and/or may carry one to three radicals from the        group consisting of C₁-C₆-alkyl and C₁-C₆-alkoxy;    -   particularly preferably    -   Q is Q¹, Q⁷, Q⁸, Q¹⁰, Q¹², Q¹³, Q²¹, Q²⁴ or Q³¹;    -   A¹, A², A³, A⁴, A⁶, A⁸, A⁹, A¹⁶ and A¹⁷ are oxygen; and    -   R³ and R⁴, R⁵ and R⁶, R⁹ and R¹⁰, R¹⁵ and R¹⁶, R¹⁸ and R¹⁹, R²⁰        and R²¹, R³⁰ and R³¹ or R⁴⁶ and R⁴⁷ together with the atoms to        which they are attached form a three- to seven-membered        heterocycle which for its part may be partially or fully        halogenated and/or may carry one to three radicals from the        group consisting of C₁-C₆-alkyl and C₁-C₆-alkoxy;    -   especially preferably    -   Q is Q⁷ or Q²¹,    -   A⁸, A⁹, A¹⁶ and A¹⁷ are oxygen;    -   R²⁹ is hydrogen, C₁-C₆-alkyl or amino; and    -   R³⁰ and R³¹ or R⁴⁶ and R⁴⁷ together with the atoms to which they        are attached form a three- to seven-membered heterocycle which        for its part may be partially or fully halogenated and/or may        carry one to three radicals from the group consisting of        C₁-C₆-alkyl and C₁-C₆-alkoxy.

Extraordinary preference is given to the compounds of the formula I.1[corresponds to formula I where X¹=fluorine; X²=chlorine; X³=hydrogen; Y=—C(A)B (where A=oxygen, B=NR²); Q=Q²¹ (where A⁸, A⁹=oxygen, R²⁹=methyl,R³⁰=trifluoromethyl and R³¹=hydrogen)], in particular to the compoundsof the formulae I.1.1 to I.1.689 of Table 1, where the definitions ofthe variables X¹, X², X³, Y, A, B, R¹, R² and Q are of particularimportance for the compounds according to the invention not only incombination with one another but in each case also on their own. TABLE 1I.1

No. R¹ R² I.1.1 CH₃ H I.1.2 C₂H₅ H I.1.3 CH₂CH₂CH₃ H I.1.4 CH₂CH₂CH₂CH₃H I.1.5 CH(CH₃)₂ H I.1.6 CH(CH₃)CH₂CH₃ H I.1.7 CH₂CH(CH₃)₂ H I.1.8C(CH₃)₃ H I.1.9 CH(CH₃)CH₂CH₂CH₃ H I.1.10 CH₂CH(CH₃)CH₂CH₃ H I.1.11CH₂CH₂CH(CH₃)₂ H I.1.12 CH₂CHF₂ H I.1.13 CH₂CF₃ H I.1.14 CH₂CH₂Cl HI.1.15 CH₂CH₂Br H I.1.16 CH₂CH₂CN H I.1.17 CH(CH₃)CN H I.1.18CH₂CH(CH₃)CN H I.1.19 cyclopropyl H I.1.20 CH₂-cyclopropyl H I.1.21cyclopentyl H I.1.22 CH₂-cyclopentyl H I.1.23 cyclohexyl H I.1.24CH₂CH═CH₂ H I.1.25 C(CH₃)═CH₂ H I.1.26 CH═CHCH₃ H I.1.27 CH₂CH═CHCH₃ HI.1.28 CH₂CF═CF₂ H I.1.29 CH₂C≡CH H I.1.30 CH(CH₃)—C≡CH H I.1.31CH₂—CO—OCH₃ H I.1.32 CH₂CH₂—CO—OCH₃ H I.1.33 CH₂—CO—OC₂H₅ H I.1.34CH(CH₃)—CO—OCH₃ H I.1.35 C(CH₃)₂—CO—OCH₃ H I.1.36 CH═CH—CO—OCH₃ H I.1.37C(CH₃)₂—CO—OCH₂—CH═CH₂ H I.1.38 CH₂CH₂OCH₃ H I.1.39 CH₂CH₂OC₂H₅ H I.1.40CH₂CH₂SCH₃ H I.1.41 CH₂CH₂S(O)CH₃ H I.1.42 CH₂CH₂SO₂CH₃ H I.1.43CH₂(1,3-dioxolanyl) H I.1.44 CH₂(2-furyl) H I.1.45 CH₂(3-furyl) H I.1.46CH₂(2-thienyl) H I.1.47 CH₂(3-thienyl) H I.1.48 phenyl H I.1.492-chlorophenyl H I.1.50 3-chlorophenyl H I.1.51 4-chlorophenyl H I.1.522-fluorophenyl H I.1.53 3-fluorophenyl H I.1.54 4-fluorophenyl H I.1.552-methylphenyl H I.1.56 3-methylphenyl H I.1.57 4-methylphenyl H I.1.582-methoxyphenyl H I.1.59 3-methoxyphenyl H I.1.60 4-methoxyphenyl HI.1.61 2-(methoxycarbonyl)phenyl H I.1.62 3-(methoxycarbonyl)phenyl HI.1.63 4-(methoxycarbonyl)phenyl H I.1.64 2-nitrophenyl H I.1.653-nitrophenyl H I.1.66 4-nitrophenyl H I.1.67 2-(dimethylamino)phenyl HI.1.68 3-(dimethylamino)phenyl H I.1.69 4-(dimethylamino)phenyl H I.1.702-(trifluoromethyl)phenyl H I.1.71 3-(trifluoromethyl)phenyl H I.1.724-(trifluoromethyl)phenyl H I.1.73 3-(phenoxy)phenyl H I.1.744-(phenoxy)phenyl H I.1.75 2,4-difluorophenyl H I.1.762,4-dichlorophenyl H I.1.77 3,4-difluorophenyl H I.1.783,4-dichlorophenyl H I.1.79 3,5-difluorophenyl H I.1.803,5-dichlorophenyl H I.1.81 2-pyridyl H I.1.82 3-pyridyl H I.1.834-pyridyl H I.1.84 α-naphthyl H I.1.84 benzyl H I.1.86 2-chlorobenzyl HI.1.87 3-chlorobenzyl H I.1.88 4-chlorobenzyl H I.1.89 2-methoxybenzyl HI.1.90 3-methoxybenzyl H I.1.91 4-methoxybenzyl H I.1.924-chloro-6-methoxy-1,3-pyrimidin-2-yl H I.1.934-methyl-6-rnethoxy-1,3-pyrimidin-2-yl H I.1.944-methyl-6-methylamino-1,3-pyrimidin-2-yl H I.1.954,6-dimethyl-1,3-pyrimidin-2-yl H I.1.964-trifluoromethyl-6-methoxy-1,3-pyrimidin-2-yl H I.1.974-methoxy-6-methylamino-1,3-pyrimidin-2-yl H I.1.984-difluoromethoxy-6-methyl-1,3-pyrimidin-2-yl H I.1.994,6-bis(difluoromethoxy)-1,3-pyrimidin-2-yl H I.1.1004-methyl-6-methoxy-1,3,5-triazin-2-yl H I.1.1014,6-dimethyl-1,3,5-triazin-2-yl H I.1.1024-methylamino-6-methoxy-1,3,5-triazin-2-yl H I.1.1034-trifluoromethyl-6-methoxy-1,3,5-triazin-2-yl H I.1.104 4,6-dimethoxy-13,5-triazin-2-yl H I.1.105 CH₃ CH₃ I.1.106 C₂H₅— CH₃ I.1.107 CH₂CH₂CH₃CH₃ I.1.108 CH₂CH₂CH₂CH₃ CH₃ I.1.109 CH(CH₃)₂ CH₃ I.1.110 CH(CH₃)C₂H₅CH₃ I.1.111 CH₂CH(CH₃)₂ CH₃ I.1.112 C(CH₃)₃ CH₃ I.1.113 CH(CH₃)CH₂CH₂CH₃CH₃ I.1.114 CH₂CH(CH₃)CH₂CH₃ CH₃ I.1.115 CH₂CH₂CH(CH₃)₂ CH₃ I.1.116CH₂CHF₂ CH₃ I.1.117 CH₂CF₃ CH₃ I.1.118 CH₂CH₂Cl CH₃ I.1.119 CH₂CH₂Br CH₃I.1.120 CH₂CH₂CN CH₃ I.1.121 CH(CH₃)CN CH₃ I.1.122 CH₂CH(CH₃)CN CH₃I.1.123 cyclopropyl CH₃ I.1.124 CH₂-cyclopropyl CH₃ I.1.125 cyclopentylCH₃ I.1.126 CH₂-cyclopentyl CH₃ I.1.127 cyclohexyl CH₃ I.1.128 CH₂CH═CH₂CH₃ I.1.129 C(CH₃)═CH₂ CH₃ I.1.130 CH═CHCH₃ CH₃ I.1.131 CH₂CH═CHCH₃ CH₃I.1.132 CH₂CF═CF₂ CH₃ I.1.133 CH₂C═CH CH₃ I.1.134 CH(CH₃)—C═CH CH₃I.1.135 OH CH₃ I.1.136 OCH₃ CH₃ I.1.137 CH₂—CO—OCH₃ CH₃ I.1.138CH₂CH₂—CO—OCH₃ CH₃ I.1.139 CH₂—CO—OC₂H₅ CH₃ I.1.140 CH(CH₃)—CO—OCH₃ CH₃I.1.141 C(CH₃)₂—CO—OCH₃ CH₃ I.1.142 CH═CH—CO—OCH₃ CH₃ I.1.143C(CH₃)₂—CO—OCH₂—CH═CH₂ CH₃ I.1.144 CH₂CH₂OCH₃ CH₃ I.1.145 CH₂CH₂OC₂H₅CH₃ I.1.146 CH₂CH₂SCH₃ CH₃ I.1.147 CH₂CH₂S(O)CH₃ CH₃ I.1.148CH₂CH₂SO₂CH₃ CH₃ I.1.149 CH₂(1,3-dioxolanyl) CH₃ I.1.150 CH₂(2-furyl)CH₃ I.1.151 CH₂(3-furyl) CH₃ I.1.152 CH₂(2-thienyl) CH₃ I.1.153CH₂(3-thienyl) CH₃ I.1.154 phenyl CH₃ I.1.155 2-chlorophenyl CH₃ I.1.1563-chlorophenyl CH₃ I.1.157 4-chlorophenyl CH₃ I.1.158 2-fluorophenyl CH₃I.1.159 3-fluorophenyl CH₃ I.1.160 4-fluorophenyl CH₃ I.1.1612-methylphenyl CH₃ I.1.162 3-methylphenyl CH₃ I.1.163 4-methylphenyl CH₃I.1.164 2-methoxyphenyl CH₃ I.1.165 3-methoxyphenyl CH₃ I.1.1664-methoxyphenyl CH₃ I.1.167 2-(methoxycarbonyl)phenyl CH₃ I.1.1683-(methoxycarbonyl)phenyl CH₃ I.1.169 4-(methoxycarbonyl)phenyl CH₃I.1.170 2-nitrophenyl CH₃ I.1.171 3-nitrophenyl CH₃ I.1.1724-nitrophenyl CH₃ I.1.173 2-(dimethylamino)phenyl CH₃ I.1.1743-(dimethylamino)phenyl CH₃ I.1.175 4-(dimethylamino)phenyl CH₃ I.1.1762-(trifluoromethyl)phenyl CH₃ I.1.177 3-(trifluoromethyl)phenyl CH₃I.1.178 4-(trifluoromethyl)phenyl CH₃ I.1.179 3-(phenoxy)phenyl CH₃I.1.180 4-(phenoxy)phenyl CH₃ I.1.181 2,4-difluorophenyl CH₃ I.1.1822,4-dichlorophenyl CH₃ I.1.183 3,4-difluorophenyl CH₃ I.1.1843,4-dichlorophenyl CH₃ I.1.185 3,5-difluorophenyl CH₃ I.1.1863,5-dichlorophenyl CH₃ I.1.187 2-pyridyl CH₃ I.1.188 3-pyridyl CH₃I.1.189 4-pyridyl CH₃ I.1.190 α-naphthyl CH₃ I.1.191 benzyl CH₃ I.1.1922-chlorobenzyl CH₃ I.1.193 3-chlorobenzyl CH₃ I.1.194 4-chlorobenzyl CH₃I.1.195 2-methoxybenzyl CH₃ I.1.196 3-methoxybenzyl CH₃ I.1.1974-methoxybenzyl CH₃ I.1.198 C₂H₅ C₂H₅ I.1.199 CH₂CH₂CH₃ C₂H₅ I.1.200CH₂CH₂CH₂CH₃ C₂H₅ I.1.201 CH(CH₃)₂ C₂H₅ I.1.202 CH(CH₃)CH₂CH₃ C₂H₅I.1.203 CH₂CH(CH₃)₂ C₂H₅ I.1.204 C(CH₃)₃ C₂H₅ I.1.205 CH(CH₃)CH₂CH₂CH₃C₂H₅ I.1.206 CH₂CH(CH₃)CH₂CH₃ C₂H₅ I.1.207 CH₂CH₂CH(CH₃)₂ C₂H₅ I.1.208CH₂CHF₂ C₂H₅ I.1.209 CH₂CF₃ C₂H₅ I.1.210 CH₂CH₂Cl C₂H₅ I.1.211 CH₂CH₂BrC₂H₅ I.1.212 CH₂CH₂CN C₂H₅ I.1.213 CH(CH₃)CN C₂H₅ I.1.214 CH₂CH(CH₃)CNC₂H₅ I.1.215 cyclopropyl C₂H₅ I.1.216 CH₂-cyclopropyl C₂H₅ I.1.217cyclopentyl C₂H₅ I.1.218 CH₂-cyclopentyl C₂H₅ I.1.219 cyclohexyl C₂H₅I.1.220 CH₂CH═CH₂ C₂H₅ I.1.221 C(CH₃)═CH₂ C₂H₅ I.1.222 CH═CHCH₃ C₂H₅I.1.223 CH₂CH═CHCH₃ C₂H₅ I.1.224 CH₂—CF═CF₂ C₂H₅ I.1.225 CH₂—C≡CH C₂H₅I.1.226 CH(CH₃)—C≡CH C₂H₅ I.1.227 OH C₂H₅ I.1.228 OCH₃ C₂H₅ I.1.229CH₂—CO—OCH₃ C₂H₅ I.1.230 CH₂—CH₂—CO—OCH₃ C₂H₅ I.1.231 CH₂—CO—OC₂H₅ C₂H₅I.1.232 CH(CH₃)—CO—OCH₃ C₂H₅ I.1.233 C(CH₃)₂—CO—OCH₃ C₂H₅ I.1.234CH═CH—CO—OCH₃ C₂H₅ I.1.235 C(CH₃)₂—CO—OCH₂—CH═CH₂ C₂H₅ I.1.236CH₂CH₂OCH₃ C₂H₅ I.1.237 CH₂CH₂OC₂H₅ C₂H₅ I.1.238 CH₂CH₂SCH₃ C₂H₅ I.1.239CH₂CH₂S(O)CH₃ C₂H₅ I.1.240 CH₂CH₂SO₂CH₃ C₂H₅ I.1.241 CH₂(1,3-dioxolanyl)C₂H₅ I.1.242 CH₂(2-furyl) C₂H₅ I.1.243 CH₂(3-furyl) C₂H₅ I.1.244CH₂(2-thienyl) C₂H₅ I.1.245 CH₂(3-thienyl) C₂H₅ I.1.246 phenyl C₂H₅I.1.247 2-chlorophenyl C₂H₅ I.1.248 3-chlorophenyl C₂H₅ I.1.2494-chlorophenyl C₂H₅ I.1.250 2-fluorophenyl C₂H₅ I.1.251 3-fluorophenylC₂H₅ I.1.252 4-fluorophenyl C₂H₅ I.1.253 2-methylphenyl C₂H₅ I.1.2543-methylphenyl C₂H₅ I.1.255 4-methylphenyl C₂H₅ I.1.256 2-methoxyphenylC₂H₅ I.1.257 3-methoxyphenyl C₂H₅ I.1.258 4-methoxyphenyl C₂H₅ I.1.2592-(methoxycarbonyl)phenyl C₂H₅ I.1.260 3-(methoxycarbonyl)phenyl C₂H₅I.1.261 4-(methoxycarbonyl)phenyl C₂H₅ I.1.262 2-nitrophenyl C₂H₅I.1.263 3-nitrophenyl C₂H₅ I.1.264 4-nitrophenyl C₂H₅ I.1.2652-(dimethylamino)phenyl C₂H₅ I.1.266 3-(dimethylamino)phenyl C₂H₅I.1.267 4-(dimethylamino)phenyl C₂H₅ I.1.268 2-(trifluoromethyl)phenylC₂H₅ I.1.269 3-(trifluoromethyl)phenyl C₂H₅ I.1.2704-(trifluoromethyl)phenyl C₂H₅ I.1.271 3-(phenoxy)phenyl C₂H₅ I.1.2724-(phenoxy)phenyl C₂H₅ I.1.273 2,4-difluorophenyl C₂H₅ I.1.2742,4-dichlorophenyl C₂H₅ I.1.275 3,4-difluorophenyl C₂H₅ I.1.2763,4-dichlorophenyl C₂H₅ I.1.277 3,5-difluorophenyl C₂H₅ I.1.2783,5-dichlorophenyl C₂H₅ I.1.279 2-pyridyl C₂H₅ I.1.280 3-pyridyl C₂H₅I.1.281 4-pyridyl C₂H₅ I.1.282 α-naphthyl C₂H₅ I.1.283 benzyl C₂H₅I.1.284 2-chlorobenzyl C₂H₅ I.1.285 3-chlorobenzyl C₂H₅ I.1.2864-chlorobenzyl C₂H₅ I.1.287 2-methoxybenzyl C₂H₅ I.1.288 3-methoxybenzylC₂H₅ I.1.289 4-methoxybenzyl C₂H₅ I.1.290 CH₂CH₂CH₃ CH₂CH₂CH₃ I.1.291CH₂CH₂CH₂CH₃ CH₂CH₂CH₃ I.1.292 CH(CH₃)₂ CH₂CH₂CH₃ I.1.293 CH(CH₃)CH₂CH₃CH₂CH₂CH₃ I.1.294 CH₂CH(CH₃)₂ CH₂CH₂CH₃ I.1.295 C(CH₃)₃ CH₂CH₂CH₃I.1.296 CH(CH₃)CH₂CH₂CH₃ CH₂CH₂CH₃ I.1.297 CH₂CH(CH₃)CH₂CH₃ CH₂CH₂CH₃I.1.298 CH₂CH₂CH(CH₃)₂ CH₂CH₂CH₃ I.1.299 CH₂CHF₂ CH₂CH₂CH₃ I.1.300CH₂CF₃ CH₂CH₂CH₃ I.1.301 CH₂CH₂Cl CH₂CH₂CH₃ I.1.302 CH₂CH₂Br CH₂CH₂CH₃I.1.303 CH₂CH₂CN CH₂CH₂CH₃ I.1.304 CH(CH₃)CN CH₂CH₂CH₃ I.1.305CH₂CH(CH₃)CN CH₂CH₂CH₃ I.1.306 cyclopropyl CH₂CH₂CH₃ I.1.307CH₂-cyclopropyl CH₂CH₂CH₃ I.1.308 cyclopentyl CH₂CH₂CH₃ I.1.309CH₂-cyclopentyl CH₂CH₂CH₃ I.1.310 cyclohexyl CH₂CH₂CH₃ I.1.311 CH₂CH═CH₂CH₂CH₂CH₃ I.1.312 C(CH₃)═CH₂ CH₂CH₂CH₃ I.1.313 CH═CHCH₃ CH₂CH₂CH₃I.1.314 CH₂CH═CHCH₃ CH₂CH₂CH₃ I.1.315 CH₂CF═CF₂ CH₂CH₂CH₃ I.1.316CH₂—C≡CH CH₂CH₂CH₃ I.1.317 CH(CH₃)—C≡CH CH₂CH₂CH₃ I.1.318 OH CH₂CH₂CH₃I.1.319 OCH₃ CH₂CH₂CH₃ I.1.320 CH₂—CO—OCH₃ CH₂CH₂CH₃ I.1.321CH₂—CH₂—CO—OCH₃ CH₂CH₂CH₃ I.1.322 CH₂—CO—OC₂H₅ CH₂CH₂CH₃ I.1.323CH(CH₃)—CO—OCH₃ CH₂CH₂CH₃ I.1.324 C(CH₃)₂—CO—OCH₃ CH₂CH₂CH₃ I.1.325CH═CH—CO—OCH₃ CH₂CH₂CH₃ I.1.326 C(CH₃)₂—CO—OCH₂—CH═CH₂ CH₂CH₂CH₃ I.1.327CH₂CH₂OCH₃ CH₂CH₂CH₃ I.1.328 CH₂CH₂OC₂H₅ CH₂CH₂CH₃ I.1.329 CH₂CH₂SCH₃CH₂CH₂CH₃ I.1.330 CH₂CH₂S(O)CH₃ CH₂CH₂CH₃ I.1.331 CH₂CH₂SO₂CH₃ CH₂CH₂CH₃I.1.332 CH₂(1,3-dioxolanyl) CH₂CH₂CH₃ I.1.333 CH₂(2-furyl) CH₂CH₂CH₃I.1.334 CH₂(3-furyl) CH₂CH₂CH₃ I.1.335 CH₂(2-thienyl) CH₂CH₂CH₃ I.1.336CH₂(3-thienyl) CH₂CH₂CH₃ I.1.337 phenyl CH₂CH₂CH₃ I.1.338 2-chlorophenylCH₂CH₂CH₃ I.1.339 3-chlorophenyl CH₂CH₂CH₃ I.1.340 4-chlorophenylCH₂CH₂CH₃ I.1.341 2-fluorophenyl CH₂CH₂CH₃ I.1.342 3-fluorophenylCH₂CH₂CH₃ I.1.343 4-fluorophenyl CH₂CH₂CH₃ I.1.344 2-methylphenylCH₂CH₂CH₃ I.1.345 3-methylphenyl CH₂CH₂CH₃ I.1.346 4-methylphenylCH₂CH₂CH₃ I.1.347 2-methoxyphenyl CH₂CH₂CH₃ I.1.348 3-methoxyphenylCH₂CH₂CH₃ I.1.349 4-methoxyphenyl CH₂CH₂CH₃ I.1.3502-(methoxycarbonyl)phenyl CH₂CH₂CH₃ I.1.351 3-(methoxycarbonyl)phenylCH₂CH₂CH₃ I.1.352 4-(methoxycarbonyl)phenyl CH₂CH₂CH₃ I.1.3532-nitrophenyl CH₂CH₂CH₃ I.1.354 3-nitrophenyl CH₂CH₂CH₃ I.1.3554-nitrophenyl CH₂CH₂CH₃ I.1.356 2-(dimethylamino)phenyl CH₂CH₂CH₃I.1.357 3-(dimethylamino)phenyl CH₂CH₂CH₃ I.1.3584-(dimethylamino)phenyl CH₂CH₂CH₃ I.1.359 2-(trifluoromethyl)phenylCH₂CH₂CH₃ I.1.360 3-(trifluoromethyl)phenyl CH₂CH₂CH₃ I.1.3614-(trifluoromethyl)phenyl CH₂CH₂CH₃ I.1.362 3-(phenoxy)phenyl CH₂CH₂CH₃I.1.363 4-(phenoxy)phenyl CH₂CH₂CH₃ I.1.364 2,4-difluorophenyl CH₂CH₂CH₃I.1.365 2,4-dichlorophenyl CH₂CH₂CH₃ I.1.366 3,4-difluorophenylCH₂CH₂CH₃ I.1.367 3,4-dichlorophenyl CH₂CH₂CH₃ I.1.3683,5-difluorophenyl CH₂CH₂CH₃ I.1.369 3,5-dichlorophenyl CH₂CH₂CH₃I.1.370 2-pyridyl CH₂CH₂CH₃ I.1.371 3-pyridyl CH₂CH₂CH₃ I.1.3724-pyridyl CH₂CH₂CH₃ I.1.373 α-naphthyl CH₂CH₂CH₃ I.1.374 benzylCH₂CH₂CH₃ I.1.375 2-chlorobenzyl CH₂CH₂CH₃ I.1.376 3-chlorobenzylCH₂CH₂CH₃ I.1.377 4-chlorobenzyl CH₂CH₂CH₃ I.1.378 2-methoxybenzylCH₂CH₂CH₃ I.1.379 3-methoxybenzyl CH₂CH₂CH₃ I.1.380 4-methoxybenzylCH₂CH₂CH₃ I.1.381 CH₂CH₂CH₂CH₃ CH(CH₃)₂ I.1.382 CH(CH₃)₂ CH(CH₃)₂I.1.383 CH(CH₃)CH₂CH₃ CH(CH₃)₂ I.1.384 CH₂CH(CH₃)₂ CH(CH₃)₂ I.1.385C(CH₃)₃ CH(CH₃)₂ I.1.386 CH(CH₃)CH₂CH₂CH₃ CH(CH₃)₂ I.1.387CH₂CH(CH₃)CH₂CH₃ CH(CH₃)₂ I.1.388 CH₂CH₂CH(CH₃)₂ CH(CH₃)₂ I.1.389CH₂CHF₂ CH(CH₃)₂ I.1.390 CH₂CF₃ CH(CH₃)₂ I.1.391 CH₂CH₂Cl CH(CH₃)₂I.1.392 CH₂CH₂Br CH(CH₃)₂ I.1.393 CH₂CH₂CN CH(CH₃)₂ I.1.394 CH(CH₃)CNCH(CH₃)₂ I.1.395 CH₂CH(CH₃)CN CH(CH₃)₂ I.1.396 cyclopropyl CH(CH₃)₂I.1.397 CH₂-cyclopropyl CH(CH₃)₂ I.1.398 cyclopentyl CH(CH₃)₂ I.1.399CH₂-cyclopentyl CH(CH₃)₂ I.1.400 cyclohexyl CH(CH₃)₂ I.1.401 CH₂CH═CH₂CH(CH₃)₂ I.1.402 C(CH₃)═CH₂ CH(CH₃)₂ I.1.403 CH═CHCH₃ CH(CH₃)₂ I.1.404CH₂CH═CHCH₃ CH(CH₃)₂ I.1.405 CH₂CF═CF₂ CH (CH₃)₂ I.1.406 CH₂—C≡CHCH(CH₃)₂ I.1.407 CH(CH₃)—C≡CH CH(CH₃)₂ I.1.408 OH CH(CH₃)₂ I.1.409 OCH₃CH(CH₃)₂ I.1.410 CH₂—CO—OCH₃ CH(CH₃)₂ I.1.411 CH₂—CH₂—CO—OCH₃ CH(CH₃)₂I.1.412 CH₂—CO—OC₂H₅ CH(CH₃)₂ I.1.413 CH(CH₃)—CO—OCH₃ CH(CH₃)₂ I.1.414C(CH₃)₂—CO—OCH₃ CH(CH₃)₂ I.1.415 CH═CH—CO—OCH₃ CH(CH₃)₂ I.1.416C(CH₃)₂—CO—OCH₂—CH═CH₂ CH(CH₃)₂ I.1.417 CH₂CH₂OCH₃ CH(CH₃)₂ I.1.418CH₂CH₂OC₂H₅ CH(CH₃)₂ I.1.419 CH₂CH₂SCH₃ CH(CH₃)₂ I.1.420 CH₂CH₂S(O)CH₃CH(CH₃)₂ I.1.421 CH₂CH₂SO₂CH₃ CH(CH₃)₂ I.1.422 CH₂(1,3-dioxolanyl)CH(CH₃)₂ I.1.423 CH₂(2-furyl) CH(CH₃)₂ I.1.424 CH₂(3-furyl) CH(CH₃)₂I.1.425 CH₂(2-thienyl) CH(CH₃)₂ I.1.426 CH₂(3-thienyl) CH(CH₃)₂ I.1.427phenyl CH(CH₃)₂ I.1.428 2-chlorophenyl CH(CH₃)₂ I.1.429 3-chlorophenylCH(CH₃)₂ I.1.430 4-chlorophenyl CH(CH₃)₂ I.1.431 2-fluorophenyl CH(CH₃)₂I.1.432 3-fluorophenyl CH(CH₃)₂ I.1.433 4-fluorophenyl CH(CH₃)₂ I.1.4342-methylphenyl CH(CH₃)₂ I.1.435 3-methylphenyl CH(CH₃)₂ I.1.4364-methylphenyl CH(CH₃)₂ I.1.437 2-methoxyphenyl CH(CH₃)₂ I.1.4383-methoxyphenyl CH(CH₃)₂ I.1.439 4-methoxyphenyl CH(CH₃)₂ I.1.4402-(methoxycarbonyl)phenyl CH(CH₃)₂ I.1.441 3-(methoxycarbonyl)phenylCH(CH₃)₂ I.1.442 4-(methoxycarbonyl)phenyl CH(CH₃)₂ I.1.4432-nitrophenyl CH(CH₃)₂ I.1.444 3-nitrophenyl CH(CH₃)₂ I.1.4454-nitrophenyl CH(CH₃)₂ I.1.446 2-(dimethylamino)phenyl CH(CH₃)₂ I.1.4473-(dimethylamino)phenyl CH(CH₃)₂ I.1.448 4-(dimethylamino)phenylCH(CH₃)₂ I.1.449 2-(trifluoromethyl)phenyl CH(CH₃)₂ I.1.4503-(trifluoromethyl)phenyl CH(CH₃)₂ I.1.451 4-(trifluoromethyl)phenylCH(CH₃)₂ I.1.452 3-(phenoxy)phenyl CH(CH₃)₂ I.1.453 4-(phenoxy)phenylCH(CH₃)₂ I.1.454 2,4-difluorophenyl CH(CH₃)₂ I.1.455 2,4-dichlorophenylCH(CH₃)₂ I.1.456 3,4-difluorophenyl CH(CH₃)₂ I.1.457 3,4-dichlorophenylCH(CH₃)₂ I.1.458 3,5-difluorophenyl CH(CH₃)₂ I.1.459 3,5-dichlorophenylCH(CH₃)₂ I.1.460 2-pyridyl CH(CH₃)₂ I.1.461 3-pyridyl CH(CH₃)₂ I.1.4624-pyridyl CH(CH₃)₂ I.1.463 α-naphthyl CH(CH₃)₂ I.1.464 benzyl CH(CH₃)₂I.1.465 2-chlorobenzyl CH(CH₃)₂ I.1.466 3-chlorobenzyl CH(CH₃)₂ I.1.4674-chlorobenzyl CH(CH₃)₂ I.1.468 2-methoxybenzyl CH(CH₃)₂ I.1.4693-methoxybenzyl CH(CH₃)₂ I.1.470 4-methoxybenzyl CH(CH₃)₂ I.1.471CH(CH₃)CH₂CH₃ CH₂CH₂CH₂CH₃ I.1.472 CH₂CH(CH₃)₂ CH₂CH₂CH₂CH₃ I.1.473C(CH₃)₃ CH₂CH₂CH₂CH₃ I.1.474 CH(CH₃)CH₂CH₂CH₃ CH₂CH₂CH₂CH₃ I.1.475CH₂CH(CH₃)CH₂CH₃ CH₂CH₂CH₂CH₃ I.1.476 CH₂CH₂CH(CH₃)₂ CH₂CH₂CH₂CH₃I.1.477 CH₂CHF₂ CH₂CH₂CH₂CH₃ I.1.478 CH₂CF₃ CH₂CH₂CH₂CH₃ I.1.479CH₂CH₂Cl CH₂CH₂CH₂CH₃ I.1.480 CH₂CH₂Br CH₂CH₂CH₂CH₃ I.1.481 CH₂CH₂CNCH₂CH₂CH₂CH₃ I.1.482 CH(CH₃)CN CH₂CH₂CH₂CH₃ I.1.483 CH₂CH(CH₃)CNCH₂CH₂CH₂CH₃ I.1.484 cyclopropyl CH₂CH₂CH₂CH₃ I.1.485 CH₂-cyclopropylCH₂CH₂CH₂CH₃ I.1.486 cyclopentyl CH₂CH₂CH₂CH₃ I.1.487 CH₂-cyclopentylCH₂CH₂CH₂CH₃ I.1.488 cyclohexyl CH₂CH₂CH₂CH₃ I.1.489 CH₂CH═CH₂CH₂CH₂CH₂CH₃ I.1.490 C(CH₃)═CH₂ CH₂CH₂CH₂CH₃ I.1.491 CH═CHCH₃CH₂CH₂CH₂CH₃ I.1.492 CH₂CH═CHCH₃ CH₂CH₂CH₂CH₃ I.1.493 CH₂CF═CF₂CH₂CH₂CH₂CH₃ I.1.494 CH₂—C≡CH CH₂CH₂CH₂CH₃ I.1.495 CH(CH₃)—C≡CHCH₂CH₂CH₂CH₃ I.1.496 OH CH₂CH₂CH₂CH₃ I.1.497 OCH₃ CH₂CH₂CH₂CH₃ I.1.498CH₂—CO—OCH₃ CH₂CH₂CH₂CH₃ I.1.499 CH₂—CH₂—CO—OCH₃ CH₂CH₂CH₂CH₃ I.1.500CH₂—CO—OC₂H₅ CH₂CH₂CH₂CH₃ I.1.501 CH(CH₃)—CO—OCH₃ CH₂CH₂CH₂CH₃ I.1.502C(CH₃)₂—CO—OCH₃ CH₂CH₂CH₂CH₃ I.1.503 CH═CH—CO—OCH₃ CH₂CH₂CH₂CH₃ I.1.504C(CH₃)₂—CO—OCH₂—CHCH₂ CH₂CH₂CH₂CH₃ I.1.505 CH₂CH₂OCH₃ CH₂CH₂CH₂CH₃I.1.506 CH₂CH₂OC₂H₅ CH₂CH₂CH₂CH₃ I.1.507 CH₂CH₂SCH₃ CH₂CH₂CH₂CH₃ I.1.508CH₂CH₂S(O)CH₃ CH₂CH₂CH₂CH₃ I.1.509 CH₂CH₂SO₂CH₃ CH₂CH₂CH₂CH₃ I.1.510CH₂(1,3-dioxolanyl) CH₂CH₂CH₂CH₃ I.1.511 CH₂(2-furyl) CH₂CH₂CH₂CH₃I.1.512 CH₂(3-furyl) CH₂CH₂CH₂CH₃ I.1.513 CH₂(2-thienyl) CH₂CH₂CH₂CH₃I.1.514 CH₂(3-thienyl) CH₂CH₂CH₂CH₃ I.1.515 phenyl CH₂CH₂CH₂CH₃ I.1.5162-chlorophenyl CH₂CH₂CH₂CH₃ I.1.517 3-chlorophenyl CH₂CH₂CH₂CH₃ I.1.5184-chlorophenyl CH₂CH₂CH₂CH₃ I.1.519 2-fluorophenyl CH₂CH₂CH₂CH₃ I.1.5203-fluorophenyl CH₂CH₂CH₂CH₃ I.1.521 4-fluorophenyl CH₂CH₂CH₂CH₃ I.1.5222-methylphenyl CH₂CH₂CH₂CH₃ I.1.523 3-methylphenyl CH₂CH₂CH₂CH₃ I.1.5244-methylphenyl CH₂CH₂CH₂CH₃ I.1.525 2-methoxyphenyl CH₂CH₂CH₂CH₃ I.1.5263-methoxyphenyl CH₂CH₂CH₂CH₃ I.1.527 4-methoxyphenyl CH₂CH₂CH₂CH₃I.1.528 2-(methoxycarbonyl)phenyl CH₂CH₂CH₂CH₃ I.1.5293-(methoxycarbonyl)phenyl CH₂CH₂CH₂CH₃ I.1.530 4-(methoxycarbonyl)phenylCH₂CH₂CH₂CH₃ I.1.531 2-nitrophenyl CH₂CH₂CH₂CH₃ I.1.532 3-nitrophenylCH₂CH₂CH₂CH₃ I.1.689 4-nitrophenyl CH₂CH₂CH₂CH₃ I.1.5342-(dimethylamino)phenyl CH₂CH₂CH₂CH₃ I.1.535 3-(dimethylamino)phenylCH₂CH₂CH₂CH₃ I.1.536 4-(dimethylamino)phenyl CH₂CH₂CH₂CH₃ I.1.5372-(trifluoromethyl)phenyl CH₂CH₂CH₂CH₃ I.1.538 3-(trifluoromethyl)phenylCH₂CH₂CH₂CH₃ I.1.539 4-(trifluoromethyl)phenyl CH₂CH₂CH₂CH₃ I.1.5403-(phenoxy)phenyl CH₂CH₂CH₂CH₃ I.1.541 4-(phenoxy)phenyl CH₂CH₂CH₂CH₃I.1.542 2,4-difluorophenyl CH₂CH₂CH₂CH₃ I.1.543 2,4-dichlorophenylCH₂CH₂CH₂CH₃ I.1.544 3,4-difluorophenyl CH₂CH₂CH₂CH₃ I.1.5453,4-dichlorophenyl CH₂CH₂CH₂CH₃ I.1.546 3,5-difluorophenyl CH₂CH₂CH₂CH₃I.1.547 3,5-dichlorophenyl CH₂CH₂CH₂CH₃ I.1.548 2-pyridyl CH₂CH₂CH₂CH₃I.1.549 3-pyridyl CH₂CH₂CH₂CH₃ I.1.550 4-pyridyl CH₂CH₂CH₂CH₃ I.1.551α-naphthyl CH₂CH₂CH₂CH₃ I.1.552 benzyl CH₂CH₂CH₂CH₃ I.1.5532-chlorobenzyl CH₂CH₂CH₂CH₃ I.1.554 3-chlorobenzyl CH₂CH₂CH₂CH₃ I.1.5554-chlorobenzyl CH₂CH₂CH₂CH₃ I.1.556 2-methoxybenzyl CH₂CH₂CH₂CH₃ I.1.5573-methoxybenzyl CH₂CH₂CH₂CH₃ I.1.558 4-methoxybenzyl CH₂CH₂CH₂CH₃I.1.559 CH(CH₃)CH₂CH₃ CH₂CH(CH₃)₂ I.1.560 CH₂CH(CH₃)₂ CH₂CH(CH₃)₂I.1.561 CH(CH₃)CH₂CH₂CH₃ CH₂CH(CH₃)₂ I.1.562 CH₂CH(CH₃)CH₂CH₃CH₂CH(CH₃)₂ I.1.563 CH₂CH₂CH(CH₃)₂ CH₂CH(CH₃)₂ I.1.564 CH₂CHF₂CH₂CH(CH₃)₂ I.1.565 CH₂CF₃ CH₂CH(CH₃)₂ I.1.566 CH₂CH₂Cl CH₂CH(CH₃)₂I.1.567 CH₂CH₂Br CH₂CH(CH₃)₂ I.1.568 CH₂CH₂CN CH₂CH(CH₃)₂ I.1.569CH(CH₃)CN CH₂CH(CH₃)₂ I.1.570 CH₂CH(CH₃)CN CH₂CH(CH₃)₂ I.1.571cyclopropyl CH₂CH(CH₃)₂ I.1.572 CH₂-cyclopropyl CH₂CH(CH₃)₂ I.1.573cyclopentyl CH₂CH(CH₃)₂ I.1.574 CH₂-cyclopentyl CH₂CH(CH₃)₂ I.1.575cyclohexyl CH₂CH(CH₃)₂ I.1.576 CH₂CH═CH₂ CH₂CH(CH₃)₂ I.1.577 C(CH₃)═CH₂CH₂CH(CH₃)₂ I.1.578 CH═CHCH₃ CH₂CH(CH₃)₂ I.1.579 CH₂CH═CHCH₃ CH₂CH(CH₃)₂I.1.580 CH₂CF═CF₂ CH₂CH(CH₃)₂ I.1.581 CH₂—C≡CH CH₂CH(CH₃)₂ I.1.582CH(CH₃)—C≡CH CH₂CH(CH₃)₂ I.1.583 OH CH₂CH(CH₃)₂ I.1.584 OCH₃ CH₂CH(CH₃)₂I.1.585 CH₂—CO—OCH₃ CH₂CH(CH₃)₂ I.1.586 CH₂—CH₂—CO—OCH₃ CH₂CH(CH₃)₂I.1.587 CH₂—CO—OC₂H₅ CH₂CH(CH₃)₂ I.1.588 CH(CH₃)—CO—OCH₃ CH₂CH(CH₃)₂I.1.589 C(CH₃)₂—CO—OCH₃ CH₂CH(CH₃)₂ I.1.590 CH═CH—CO—OCH₃ CH₂CH(CH₃)₂I.1.591 C(CH₃)₂—CO—OCH₂—CH═CH₂ CH₂CH(CH₃)₂ I.1.592 CH₂CH₂OCH₃CH₂CH(CH₃)₂ I.1.593 CH₂CH₂OC₂H₅ CH₂CH(CH₃)₂ I.1.594 CH₂CH₂SCH₃CH₂CH(CH₃)₂ I.1.595 CH₂CH₂S(O)CH₃ CH₂CH(CH₃)₂ I.1.596 CH₂CH₂SO₂CH₃CH₂CH(CH₃)₂ I.1.597 CH(CH₃)C₂H₅ CH(CH₃)CH₂CH₃ I.1.598 CH(CH₃)CH₂CH₂CH₃CH(CH₃)CH₂CH₃ I.1.599 CH₂CH(CH₃)CH₂CH₃ CH(CH₃)CH₂CH₃ I.1.600CH₂CH₂CH(CH₃)₂ CH(CH₃)CH₂CH₃ I.1.601 CH₂CHF₂ CH(CH₃)CH₂CH₃ I.1.602CH₂CF₃ CH(CH₃)CH₂CH₃ I.1.603 CH₂CH—Cl CH(CH₃)CH₂CH₃ I.1.604 CH₂CH₂BrCH(CH₃)CH₂CH₃ I.1.605 CH₂CH₂CN CH(CH₃)CH₂CH₃ I.1.606 CH(CH₃)CNCH(CH₃)CH₂CH₃ I.1.607 CH₂CH(CH₃)CN CH(CH₃)CH₂CH₃ I.1.608 cyclopropylCH(CH₃)CH₂CH₃ I.1.609 CH₂—cyclopropyl CH(CH₃)CH₂CH₃ I.1.610 cyclopentylCH(CH₃)CH₂CH₃ I.1.611 CH₂-cyclopentyl CH(CH₃)CH₂CH₃ I.1.612 cyclohexylCH(CH₃)CH₂CH₃ I.1.613 CH₂CH═CH₂ CH(CH₃)CH₂CH₃ I.1.614 C(CH₃)═CH₂CH(CH₃)CH₂CH₃ I.1.615 CH═CHCH₃ CH(CH₃)CH₂CH₃ I.1.616 CH₂CH═CHCH₃CH(CH₃)CH₂CH₃ I.1.617 CH₂CF═CF₂ CH(CH₃)CH₂CH₃ I.1.618 CH₂—C≡CHCH(CH₃)CH₂CH₃ I.1.619 CH(CH₃)—C≡CH CH(CH₃)CH₂CH₃ I.1.620 OHCH(CH₃)CH₂CH₃ I.1.621 OCH₃ CH(CH₃)CH₂CH₃ I.1.622 CH₂—CO—OCH₃CH(CH₃)CH₂CH₃ I.1.623 CH₂—CH₂—CO—OCH₃ CH(CH₃)CH₂CH₃ I.1.624 CH₂—CO—OC₂H₅CH(CH₃)CH₂CH₃ I.1.625 CH(CH₃)—CO—OCH₃ CH(CH₃)CH₂CH₃ I.1.626C(CH₃)₂—CO—OCH₃ CH(CH₃)CH₂CH₃ I.1.627 CH═CH—CO—OCH₃ CH(CH₃)CH₂CH₃I.1.628 C(CH₃)₂—CO—OCH₂—CH═CH₂ CH(CH₃)CH₂CH₃ I.1.629 CH₂CH₂OCH₃CH(CH₃)CH₂CH₃ I.1.630 CH₂CH₂OC₂H₅ CH(CH₃)CH₂CH₃ I.1.631 CH₂CH₂SCH₃CH(CH₃)CH₂CH₃ I.1.632 CH₂CH₂S(O)CH₃ CH(CH₃)CH₂CH₃ I.1.633 CH₂CH₂SO₂CH₃CH(CH₃)CH₂CH₃ I.1.634 CH(CH₃)C₂H₅ C(CH₃)₃ I.1.635 CH₂CH(CH₃)₂ C(CH₃)₃I.1.636 C(CH₃)₃ C(CH₃)₃ I.1.637 CH(CH₃)CH₂CH₂CH₃ C(CH₃)₃ I.1.638CH₂CH(CH₃)CH₂CH₃ C(CH₃)₃ I.1.639 CH₂CH₂CH(CH₃)₂ C(CH₃)₃ I.1.640 CH₂CHF₂C(CH₃)₃ I.1.641 CH₂CF₃ C(CH₃)₃ I.1.642 CH₂CH₂Cl C(CH₃)₃ I.1.643 CH₂CH₂BrC(CH₃)₃ I.1.644 CH₂CH₂CN C(CH₃)₃ I.1.645 CH(CH₃)CN C(CH₃)₃ I.1.646CH₂CH(CH₃)CN C(CH₃)₃ I.1.647 cyclopropyl C(CH₃)₃ I.1.648 CH₂-cyclopropylC(CH₃)₃ I.1.649 cyclopentyl C(CH₃)₃ I.1.650 CH₂-cyclopentyl C(CH₃)₃I.1.651 cyclohexyl C(CH₃)₃ I.1.652 CH₂CH═CH₂ C(CH₃)₃ I.1.653 C(CH₃)═CH₂C(CH₃)₃ I.1.654 CH═CHCH₃ C(CH₃)₃ I.1.655 CH₂CH═CHCH₃ C(CH₃)₃ I.1.656CH₂CF═CF₂ C(CH₃)₃ I.1.657 CH₂—C≡CH C(CH₃)₃ I.1.658 CH(CH₃)—C≡CH C(CH₃)₃I.1.659 OH C(CH₃)₃ I.1.660 OCH₃ C(CH₃)₃ I.1.661 CH₂—CO—OCH₃ C(CH₃)₃I.1.662 CH₂—CH₂—CO—OCH₃ C(CH₃)₃ I.1.663 CH₂—CO—OC₂H₅ C(CH₃)₃ I.1.664CH(CH₃)—CO—OCH₃ C(CH₃)₃ I.1.665 C(CH₃)₂—CO—OCH₃ C(CH₃)₃ I.1.666CH═CH—CO—OCH₃ C(CH₃)₃ I.1.667 C(CH₃)₂—CO—OCH₂—CHCH₂ C(CH₃)₃ I.1.668CH₂CH₂OCH₃ C(CH₃)₃ I.1.669 CH₂CH₂OC₂H₅ C(CH₃)₃ I.1.670 CH₂CH₂SCH₃C(CH₃)₃ I.1.671 CH₂CH₂S(O)CH₃ C(CH₃)₃ I.1.672 CH₂CH₂—SO₂—CH₃ C(CH₃)₃I.1.673 —CH₂—CH₂—CH₂—CH₂— I.1.674 —CH₂—CH₂—CH₂—CH₂—CH₂— I.1.675—CH₂—CH₂—CH₂—CH₂—CH(CH₃)— I.1.676 —CH₂—CH₂—CH₂—CH(CH₃)—CH₂— I.1.677—CH₂—CH₂—CH(CH₃)—CH₂—CH₂— I.1.678 —CH₂—CH₂—CH₂—CH₂—CH(CH₂CH₂Cl)- I.1.679—CH₂—CH₂—CH₂—CH(CH₂CH₂Cl)—CH₂— I.1.680 —CH₂—CH₂—CH(CH₂CH₂Cl)—CH₂—CH₂—I.1.681 —CH═CH—CH₂—CH₂— I.1.682 —CH₂—CH═CH—CH₂— I.1.683—CH═CH—CH₂—CH₂—CH₂— I.1.684 CH₂—CH═CH═CH₂—CH₂— I.1.685—CH₂—CH₂—O—CH₂—CH₂— I.1.686 —CH₂—CH₂—O—CH(CH₃)—CH₂— I.1.687—CH₂—CH₂—O—CH₂—CH(CH₃)— I.1.688 —CH₂—CH(CH₃)—O—CH(CH₃)—CH₂— I.1.689—CH₂—CH₂—N(CH₃)—CH₂—CH₂—

Extraordinary preference is also given to the compounds of the formulaI.2, in particular to the compounds of the formulae I.2.1 to I.2.689which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is oxygen.

Extraordinary preference is also given to the compounds of the formulaI.3, in particular to the compounds of the formulae I.3.1 to I.3.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is sulfur.

Extraordinary preference is also given to the compounds of the formulaI.4, in particular to the compounds of the formulae I.4.1 to I.4.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is a bond.

Extraordinary preference is also given to the compounds of the formulaI.5, in particular to the compounds of the formulae I.5.1 to I.5.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂.

Extraordinary preference is also given to the compounds of the formulaI.6, in particular to the compounds of the formulae I.6.1 to I.6.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂NR².

Extraordinary preference is also given to the compounds of the formulaI.7, in particular to the compounds of the formulae I.7.1 to I.7.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formulaI.8, in particular to the compounds of the formulae I.8.1 to I.8.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is oxygen and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formulaI.9, in particular to the compounds of the formulae I.9.1 to I.9.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is sulfur and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formulaI.10, in particular to the compounds of the formulae I.10.1 to I.10.689,which differ from the corresponding compounds of the formulae 1;1.1 toI.1.689 in that B is a bond and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formulaI.11, in particular to the compounds of the formulae I.11.1 to I.11.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂ and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formulaI.12, in particular to the compounds of the formulae I.12.1 to I.12.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂NR² and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formulaI.13, in particular to the compounds of the formulae I.13.1 to I.13.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is hydrogen.

Extraordinary preference is also given to the compounds of the formulaI.14, in particular to the compounds of the formulae I.14.1 to I.14.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is hydrogen and B is oxygen.

Extraordinary preference is also given to the compounds of the formulaI.15, in particular to the compounds of the formulae I.15.1 to I.15.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is hydrogen and B is sulfur.

Extraordinary preference is also given to the compounds of the formulaI.16, in particular to the compounds of the formulae I.16.1 to I.16.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is hydrogen and B is a bond.

Extraordinary preference is also given to the compounds of the formulaI.17, in particular to the compounds of the formulae I.17.1 to I.17.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is hydrogen and Y is SO₂.

Extraordinary preference is also given to the compounds of the formulaI.18, in particular to the compounds of the formulae I.18.1 to I.18.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is hydrogen and Y is SO₂NR².

Extraordinary preference is also given to the compounds of the formulaI.19, in particular to the compounds of the formulae I.19.1 to I.19.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is hydrogen and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formulaI.20, in particular to the compounds of the formulae I.20.1 to I.20.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is hydrogen, B is oxygen and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formulaI.21, in particular to the compounds of the formulae I.21.1 to I.21.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is hydrogen, B is sulfur and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formulaI.22, in particular to the compounds of the formulae I.22.1 to I.22.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is hydrogen, B is a bond and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formulaI.23, in particular to the compounds of the formulae I.23.1 to I.23.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is hydrogen, Y is SO₂ and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formulaI.24, in particular to the compounds of the formulae I.24.1 to I.24.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is hydrogen, Y is SO₂NR² and R²⁹ is amino.

Extraordinary preference is also given to the compounds of the formulaI.25, in particular to the compounds of the formulae I.25.1 to I.25.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Q is Q⁵ (where A¹=oxygen, R⁷=difluoromethyl andR⁸=methyl).

Extraordinary preference is also given to the compounds of the formulaI.26, in particular to the compounds of the formulae I.26.1 to I.26.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is oxygen and Q is Q⁵ (where A¹=oxygen,R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formulaI.27, in particular to the compounds of the formulae I.27.1 to I.27.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is sulfur and Q is Q⁵ (where A¹=oxygen,R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formulaI.28, in particular to the compounds of the formulae I.28.1 to I.28.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is a bond and Q is Q⁵ (where A¹=oxygen,R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formulaI.29, in particular to the compounds of the formulae I.29.1 to I.29.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂ and Q is Q⁵ (where A¹=oxygen, R⁷=difluoromethyland R⁸=methyl).

Extraordinary preference is also given to the compounds of the formulaI.30, in particular to the compounds of the formulae I.30.1 to I.30.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂NR² and Q is Q⁵ (where A¹=oxygen,R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formulaI.31, in particular to the compounds of the formulae I.31.1 to I.31.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is chlorine and Q is Q⁵ (where A¹=oxygen,R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formulaI.32, in particular to the compounds of the formulae I.32.1 to I.32.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is chlorine, B is oxygen and Q is Q⁵ (whereA¹=oxygen, R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formulaI.33, in particular to the compounds of the formulae I.33.1 to I.33.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is chlorine, B is sulfur and Q is Q⁵ (whereA¹=oxygen, R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formulaI.34, in particular to the compounds of the formulae I.34.1 to I.34.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is chlorine, B is a bond and Q is Q⁵ (whereA¹=oxygen, R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formulaI.35, in particular to the compounds of the formulae I.35.1 to I.35.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is chlorine, Y is SO₂ and Q is Q⁵ (where A¹=oxygen,R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formulaI.36, in particular to the compounds of the formulae I.36.1 to I.36.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is chlorine, Y is SO₂NR² and Q is Q⁵ (whereA¹=oxygen, R⁷=difluoromethyl and R⁸=methyl).

Extraordinary preference is also given to the compounds of the formulaI.37, in particular to the compounds of the formulae I.37.1 to I.37.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Q is Q²² (where A¹⁰ and A¹¹=oxygen, A¹²=sulfur and R³²,R³³=methyl).

Extraordinary preference is also given to the compounds of the formulaI.38, in particular to the compounds of the formulae I.38.1 to I.38.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is oxygen and Q is Q²² (where A¹⁰ and A¹¹=oxygen,A¹²=sulfur and R³², R³³=methyl).

Extraordinary preference is also given to the compounds of the formulaI.39, in particular to the compounds of the formulae I.39.1 to I.39.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is sulfur and Q is Q²² (where A¹⁰ and A¹¹=oxygen,A¹²=sulfur and R³², R³³=methyl).

Extraordinary preference is also given to the compounds of the formulaI.40, in particular to the compounds of the formulae I.40.1 to I.40.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is a bond and Q is Q²² (where A¹⁰ and A¹¹=oxygen,A¹²=sulfur and R³², R³³=methyl).

Extraordinary preference is also given to the compounds of the formulaI.41, in particular to the compounds of the formulae I.41.1 to I.41.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂ and Q is Q²² (where A¹⁰ and A¹¹=oxygen,A¹²=sulfur and R³² R³³=methyl).

Extraordinary preference is also given to the compounds of the formulaI.42, in particular to the compounds of the formulae I.42.1 to I.42.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂NR² and Q is Q²² (where A¹⁰ and A¹¹=oxygen,A¹²=sulfur and R³², R³³=methyl).

Extraordinary preference is also given to the compounds of the formulaI.43, in particular to the compounds of the formulae I.43.1 to I.43.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Q is Q²² (where A¹⁰, A¹¹, A¹²=oxygen and R³²,R³³=methyl).

Extraordinary preference is also given to the compounds of the formulaI.44, in particular to the compounds of the formulae I.44.1 to I.44.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is oxygen and Q is Q²² (where A¹⁰, A¹¹, A¹²=oxygen andR³², R³³=methyl).

Extraordinary preference is also given to the compounds of the formulaI.45, in particular to the compounds of the formulae I.45.1 to I.45.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is sulfur and Q is Q²² (where A¹⁰, A¹¹, A¹²=oxygen andR³², R³³=methyl).

Extraordinary preference is also given to the compounds of the formulaI.46, in particular to the compounds of the formulae I.46.1 to I.46.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is a bond and Q is Q²² (where A¹⁰, A¹¹, A¹²=oxygen andR³² R³³=methyl).

Extraordinary preference is also given to the compounds of the formulaI.47, in particular to the compounds of the formulae I.47.1 to I.47.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂ and Q is Q²² (where A¹⁰, A¹¹, A¹²=oxygen andR³², R³³=methyl).

Extraordinary preference is also given to the compounds of the formulaI.48, in particular to the compounds of the formulae I.48.1 to I.48.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂NR² and Q is Q²² (where A¹⁰, A¹¹, A¹²=oxygen andR³², R³³=methyl).

Extraordinary preference is also given to the compounds of the formulaI.49, in particular to the compounds of the formulae I.49.1 to I.49.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Q is Q²⁷ (where A¹³=oxygen, R³⁴, R³⁶=hydrogen,R³⁵=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formulaI.50, in particular to the compounds of the formulae I.50.1 to I.50.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is oxygen and Q is Q²⁷ (where A¹³=oxygen, R³⁴,R³⁶=hydrogen, R³⁵=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formulaI.51, in particular to the compounds of the formulae I.51.1 to I.51.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is sulfur and Q is Q²⁷ (where A¹³=oxygen, R³⁴,R³⁶=hydrogen, R³⁵=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formulaI.52, in particular to the compounds of the formulae I.52.1 to I.52.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is a bond and Q is Q (where A¹³=oxygen, R³⁴,R³⁶=hydrogen, R³⁵=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formulaI.53, in particular to the compounds of the formulae I.53.1 to I.53.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂ and Q is Q²⁷ (where A¹³=oxygen, R³⁴,R³⁶=hydrogen, R³⁵=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formulaI.54, in particular to the compounds of the formulae I.54.1 to I.54.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂NR² and Q is Q²⁷ (where A¹³=oxygen, R³⁴,R³⁶=hydrogen, R³⁵=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formulaI.55, in particular to the compounds of the formulae I.55.1 to I.55.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Q is Q²⁷ (where A¹³=oxygen, R³⁴=hydrogen,R³⁵=trifluoromethyl, R³⁶=methyl).

Extraordinary preference is also given to the compounds of the formulaI.56, in particular to the compounds of the formulae I.56.1 to I.56.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is oxygen and Q is Q²⁷ (where A¹³=oxygen,R³⁴=hydrogen, R³⁵=trifluoromethyl, R³⁶=methyl).

Extraordinary preference is also given to the compounds of the formulaI.57, in particular to the compounds of the formulae I.57.1 to I.57.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is sulfur and Q is Q²⁷ (where A¹³=oxygen,R³⁴=hydrogen, R³⁵=trifluoromethyl, R³⁶=methyl).

Extraordinary preference is also given to the compounds of the formulaI.58, in particular to the compounds of the formulae I.58.1 to I.58.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is a bond and Q is Q²⁷ (where A¹³=oxygen,R³⁴=hydrogen, R³⁵=trifluoromethyl, R³⁶=methyl).

Extraordinary preference is also given to the compounds of the formulaI.59, in particular to the compounds of the formulae I.59.1 to I.59.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂ and Q is Q²⁷ (where A¹³=oxygen, R³⁴=hydrogen,R³⁵=trifluoromethyl, R³⁶=methyl).

Extraordinary preference is also given to the compounds of the formulaI.60, in particular to the compounds of the formulae I.60.1 to I.60.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂NR² and Q is Q²⁷ (where A¹³=oxygen,R³⁴=hydrogen, R³⁵=trifluoromethyl, R³⁶=methyl).

Extraordinary preference is also given to the compounds of the formulaI.61, in particular to the compounds of the formulae I.61.1 to I.61.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂NR² and Q is Q²⁷ (where A¹³=oxygen,R³⁴=hydrogen, R³⁵=methylsulfonyl, R³⁶=amino).

Extraordinary preference is also given to the compounds of the formulaI.62, in particular to the compounds of the formulae I.62.1 to I.62.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is oxygen and Q is Q²⁷ (where A¹³=oxygen,R³⁴=hydrogen, R³⁵=methylsulfonyl, R³⁶=amino).

Extraordinary preference is also given to the compounds of the formulaI.63, in particular to the compounds of the formulae I.63.1 to I.63.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is sulfur and Q is Q²⁷ (where A¹³=oxygen,R³⁴=hydrogen, R³⁵=methylsulfonyl, R³⁶=amino).

Extraordinary preference is also given to the compounds of the formulaI.64, in particular to the compounds of the formulae I.64.1 to I.64.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is a bond and Q is Q²⁷ (where A¹³=oxygen,R³⁴=hydrogen, R³⁵=methylsulfonyl, R³⁶=amino).

Extraordinary preference is also given to the compounds of the formulaI.65, in particular to the compounds of the formulae I.65.1 to I.65.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂ and Q is Q²⁷ (where A¹³=oxygen, R³⁴=hydrogen,R³⁵=methylsulfonyl, R³⁶=amino).

Extraordinary preference is also given to the compounds of the formulaI.66, in particular to the compounds of the formulae I.66.1 to I.66.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂NR² and Q is Q²⁷ (where A¹³=oxygen,R³⁴=hydrogen, R³⁵=methylsulfonyl, R³⁶=amino).

Extraordinary preference is also given to the compounds of the formulaI.67, in particular to the compounds of the formulae I.67.1 to I.67.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Q is Q³² (where R³⁷=chlorine, R³⁸=difluoromethoxy,R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.68, in particular to the compounds of the formulae I.68.1 to I.68.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is oxygen and Q is Q³² (where R³⁷=chlorine,R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.69, in particular to the compounds of the formulae I.69.1 to I.69.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is sulfur and Q is Q³² (where R³⁷=chlorine,R³⁸=difluoromethoxy, R³⁹ methyl).

Extraordinary preference is also given to the compounds of the formulaI.70, in particular to the compounds of the formulae I.70.1 to I.70.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is a bond and Q is Q³² (where R³⁷=chlorine,R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.71, in particular to the compounds of the formulae I.71.1 to I.71.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂ and Q is Q³² (where R³⁷=chlorine,R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.72, in particular to the compounds of the formulae 1:72.1 to I.72.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂NR² and Q is Q³² (where R³⁷=chlorine,R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.73, in particular to the compounds of the formulae I.73.1 to I.73.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Q is Q³² (where R³⁷=bromine, R³⁸=difluoromethoxy,R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.74, in particular to the compounds of the formulae I.74.1 to I.74.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is oxygen and Q is Q³² (where R³⁷=bromine,R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.75, in particular to the compounds of the formulae I.75.1 to I.75.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is sulfur and Q is Q³² (where R³⁷=bromine,R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.76, in particular to the compounds of the formulae I.76.1 to I.76.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is a bond and Q is Q³² (where R³⁷=bromine,R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.77, in particular to the compounds of the formulae I.77.1 to I.77.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂ and Q is Q³² (where R³⁷=bromine,R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.78, in particular to the compounds of the formulae I.78.1 to I.78.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂NR² and Q is Q³² (where R³⁷=bromine,R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.79, in particular to the compounds of the formulae I.79.1 to I.79.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is chlorine and Q is Q³² (where R³⁷=bromine,R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.80, in particular to the compounds of the formulae I.80.1 to I.80.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is chlorine, B is oxygen and Q is Q³² (whereR³⁷=bromine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.81, in particular to the compounds of the formulae I.81.1 to I.81.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is chlorine, B is sulfur and Q is Q³² (whereR³⁷=bromine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.82, in particular to the compounds of the formulae I.82.1 to I.82.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is chlorine, B is a bond and Q is Q³² (whereR³1=bromine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.83, in particular to the compounds of the formulae I.83.1 to I.83.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is chlorine, Y is SO₂ and Q is Q³² (whereR³⁷=bromine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.84, in particular to the compounds of the formulae I.84.1 to I.84.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is chlorine, Y is SO₂NR² and Q is Q³² (whereR³⁷=bromine, R³⁸=difluoromethoxy, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.85, in particular to the compounds of the formulae I.85.1 to I.85.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Q is Q³² (where R³⁷=chlorine, R³⁸=trifluoromethyl,R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.86, in particular to the compounds of the formulae I.86.1 to I.86.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is oxygen and Q is Q³² (where R³⁷=chlorine,R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.87, in particular to the compounds of the formulae I.87.1 to I.87.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is sulfur and Q is Q³² (where R³⁷=chlorine,R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.88, in particular to the compounds of the formulae I.88.1 to I.88.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is a bond and Q is Q³² (where R³⁷=chlorine,R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.89, in particular to the compounds of the formulae I.89.1 to I.89.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂ and Q is Q³² (where R³⁷=chlorine,R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.90, in particular to the compounds of the formulae I.90.1 to I.90.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂NR² and Q is Q³² (where R³⁷=chlorine,R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.91, in particular to the compounds of the formulae I.91.1 to I.91.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Q is Q³² (where R³⁷=bromine, R³⁸=trifluoromethyl,R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.92, in particular to the compounds of the formulae I.92.1 to I.92.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is oxygen and Q is Q³² (where R³⁷=bromine,R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.93, in particular to the compounds of the formulae I.93.1 to I.93.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is sulfur and Q is Q³² (where R³⁷=bromine,R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.94, in particular to the compounds of the formulae I.94.1 to I.94.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that B is a bond and Q is Q³² (where R³⁷=bromine,R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.95, in particular to the compounds of the formulae I.95.1 to I.95.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂ and Q is Q³² (where R³⁷=bromine,R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.96, in particular to the compounds of the formulae I.96.1 to I.96.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that Y is SO₂NR² and Q is Q³² (where R³⁷=bromine,R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.97, in particular to the compounds of the formulae I.97.1 to I.97.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is chlorine and Q is Q³² (where R³⁷=bromine,R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.98, in particular to the compounds of the formulae I.98.1 to I.98.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is chlorine, B is oxygen and Q is Q³² (whereR³⁷=bromine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.99, in particular to the compounds of the formulae I.99.1 to I.99.689,which differ from the corresponding compounds of the formulae I.1.1 toI.1.689 in that X¹ is chlorine, B is sulfur and Q is Q³² (whereR³⁷=bromine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.100, in particular to the compounds of the formulae I.100.1 toI.100.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that X¹ is chlorine, B is a bond and Q is Q³² (whereR³⁷=bromine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.101, in particular to the compounds-of the formulae I.101.1 toI.101.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that X¹ is chlorine, Y is SO₂ and Q is Q³² (whereR³⁷=bromine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.102, in particular to the compounds of the formulae I.102.1 toI.102.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that X¹ is chlorine, Y is SO₂NR² and Q is Q³² (whereR³⁷=bromine, R³⁸=trifluoromethyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.103, in particular to the compounds of the formulae I.103.1 toI.103.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Q is Q³² (where R³⁷=chlorine,R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.104, in particular to the compounds of the formulae I.104.1 toI.104.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is oxygen and Q is Q³² (where R³⁷=chlorine,R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.105, in particular to the compounds of the formulae I.105.1 toI.105.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is sulfur and Q is Q³² (where R³⁷=chlorine,R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.106, in particular to the compounds of the formulae I.106.1 toI.106.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is a bond and Q is Q³² (where R³⁷=chlorine,R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.107, in particular to the compounds of the formulae I.107.1 toI.107.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Y is SO₂ and Q is Q³² (where R³⁷=chlorine,R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.108, in particular to the compounds of the formulae I.108.1 toI.108.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q³² (where R³⁷=chlorine,R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.109, in particular to the compounds of the formulae I.109.1 toI.109.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Q is Q³² (where R³⁷=bromine,R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formula 1.110, in particular to the compounds of the formulae I.110.1 toI.110.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is oxygen and Q is Q³² (where R³⁷=bromine,R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.111, in particular to the compounds of the formulae I.111.1 toI.111.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is sulfur and Q is Q³² (where R³⁷=bromine,R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.112, in particular to the compounds of the formulae I.112.1 toI.112.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is a bond and Q is Q³² (where R³⁷=bromine,R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.113, in particular to the compounds of the formulae I.113.1 toI.113.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Y is SO₂ and Q is Q³² (where R³⁷=bromine,R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.114, in particular to the compounds of the formulae I.114.1 to 1.114.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q³² (where R³⁷=bromine,R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI. 115, in particular to the compounds of the formulae I.115.1 toI.115.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that X¹ is chlorine and Q is Q³² (where R³⁷=bromine,R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.116, in particular to the compounds of the formulae I.116.1 toI.116.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that X¹ is chlorine, B is oxygen and Q is Q³² (whereR³⁷=bromine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.117, in particular to the compounds of the formulae I.117.1 toI.117.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that X¹ is chlorine, B is sulfur and Q is Q³² (whereR³⁷=bromine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.118, in particular to the compounds of the formulae l.118.1 toI.118.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that X¹ is chlorine, B is a bond and Q is Q³² (whereR³⁷=bromine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.119, in particular to the compounds of the formulae I.119.1 toI.119.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that X¹ is chlorine, Y is SO₂ and Q is Q³² (whereR³⁷=bromine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.120, in particular to the compounds of the formulae I.120.1 toI.120.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that X¹ is chlorine, Y is SO₂NR² and Q is Q³² (whereR³⁷=bromine, R³⁸=methylsulfonyl, R³⁹=methyl).

Extraordinary preference is also given to the compounds of the formulaI.121, in particular to the compounds of the formulae I.121.1 toI.121.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Q is Q³⁸ (where R⁴⁰=chlorine, R⁴¹,R⁴³=hydrogen, R⁴²=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formulaI.122, in particular to the compounds of the formulae I.122.1 toI.122.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is oxygen and Q is Q³⁸ (where R⁴⁰=chlorine,R⁴¹, R⁴³=hydrogen, R⁴²=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formulaI.123, in particular to the compounds of the formulae I.123.1 toI.123.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is sulfur and Q is Q³⁸ (where R⁴⁰=chlorine,R⁴¹, R⁴³=hydrogen, R⁴²=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formulaI.124, in particular to the compounds of the formulae I.124.1 toI.124.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is a bond and Q is Q³⁸ (where R⁴⁰=chlorine,R⁴¹, R⁴³=hydrogen, R⁴²=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formulaI.125, in particular to the compounds of the formulae I.125.1 toI.125.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Y is SO₂ and Q is Q³⁸ (where R⁴⁰=chlorine, R⁴¹,R⁴³=hydrogen, R⁴²=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formulaI.126, in particular to the compounds of the formulae I.126.1 toI.126.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q³⁸ (where R⁴⁰=chlorine,R⁴¹, R⁴³=hydrogen, R⁴²=trifluoromethyl).

Extraordinary preference is also given to the compounds of the formulaI.127, in particular to the compounds of the formulae I.127.1 toI.127.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Q is Q³⁹ (where A¹=oxygen, A¹⁵=sulfur, R⁴⁴,R⁴⁵=methyl).

Extraordinary preference is also given to the compounds of the formulaI.128, in particular to the compounds of the formulae l.128.1 toI.128.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is oxygen and Q is Q³⁹ (where A¹ oxygen,A¹⁵=sulfur, R⁴⁴, R⁴⁵=methyl).

Extraordinary preference is also given to the compounds of the formulaI.129, in particular to the compounds of the formulae I.129.1 to 1.129.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is sulfur and Q is Q³⁹ (where A¹=-oxygen,A¹⁵=sulfur, R^(44,) R⁴⁵=methyl).

Extraordinary preference is also given to the compounds of the formulaI.130, in particular to the compounds of the formulae I.130.1 toI.130.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is a bond and Q is Q³⁹ (where A¹=oxygen,A¹⁵=sulfur, R⁴⁴, R⁴⁵=methyl).

Extraordinary preference is also given to the compounds of the formulaI.131, in particular to the compounds of the formulae I.131.1 toI.131.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Y is SO₂ and Q is Q³⁹ (where A¹=oxygen,A¹⁵=sulfur, R^(44,) R⁴⁵=methyl).

Extraordinary preference is also given to the compounds of the formulaI.132, in particular to the compounds of the formulae I .132.1 to 1.132.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q³⁹ (where A¹=oxygen,A¹⁵=sulfur, R^(44,) R⁴⁵=methyl).

Extraordinary preference is also given to the compounds of the formulaI.133, in particular to the compounds of the formulae I.133.1 toI.133.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Q is Q⁷ (where A¹⁶, A¹⁷=oxygen and R⁴⁶, R⁴⁷form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.134, in particular to the compounds of the formulae I.134.1 toI.134.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is oxygen and Q is Q⁷ (where A¹⁶, A¹⁷=oxygenand R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.135, in particular to the compounds of the formulae I.135.1 toI.135.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is sulfur and Q is Q⁷ (where A¹⁶, A¹⁷=oxygenand R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.136, in particular to the compounds of the formulae I.136.1 toI.136.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is a bond and Q is Q⁷ (where A¹⁶, A¹⁷=oxygenand R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.137, in particular to the compounds of the formulae I.137.1 toI.137.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Y is SO₂ and Q is Q⁷ (where A¹⁶, A¹⁷=oxygen andR⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.138, in particular to the compounds of the formulae I.138.1 toI.138.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q⁷ (where A¹⁶, A¹⁷=oxygenand R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.139, in particular to the compounds of the formulae I. 139.1 toI.139.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Q is Q⁷ (where A¹⁶=sulfur, A¹⁷=oxygen andR^(46,) R⁴⁷ form a chain —H₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.140, in particular to the compounds of the formulae I.140.1 toI.140.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is oxygen and Q is Q⁷ (where A¹⁶=sulfur,A¹⁷=oxygen and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.141, in particular to the compounds of the formulae I.141.1 toI.141.689, which differ from the corresponding compounds of-the formulaeI.1.1 to I.1.689 in that B is sulfur and Q is Q⁷ (where A¹⁶=sulfur,A¹⁷=oxygen and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.142, in particular to the compounds of the formulae I.142.1 toI.142.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is a bond and Q is Q⁷ (where A¹⁶=sulfur,A¹⁷=oxygen and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.143, in particular to the compounds of the formulae I.143.1 toI.143.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Y is SO₂ and Q is Q⁷ (where A¹⁶=sulfur,A¹⁷=oxygen and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.144, in particular to the compounds of the formulae I.144.1 toI.144.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q⁷ (where A¹⁶=sulfur,A¹⁷=oxygen and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.145, in particular to the compounds of the formulae I.145.1 toI.145.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Q is Q⁷ (where A¹⁶, A¹⁷=sulfur and R⁴⁶, R⁴⁷form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.146, in particular to the compounds of the formulae I.146.1 toI.146.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is oxygen and Q is Q⁷ (where A¹⁶, A¹⁷=sulfurand R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.147, in particular to the compounds of the formulae I. 147.1 to I.147.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is sulfur and Q is Q⁷ (where A¹⁶, A¹⁷=sulfurand R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.148, in particular to the compounds of the formulae I.148.1 toI.148.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is a bond and Q is Q⁷ (where A¹⁶, A¹⁷=sulfurand R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.149, in particular to the compounds of the formulae I.149.1 to1-.149.689, which differ from the corresponding compounds of theformulae I.1.1 to I.1.689 in that Y is SO₂ and Q is Q⁷ (where A¹⁶,A¹⁷=sulfur and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.150, in particular to the compounds of the formulae I.150.1 toI.150.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q⁷ (where A¹⁶, A¹⁷=sulfurand R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.151, in particular to the compounds of the formulae I.151.1 toI.151.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Q is Q⁷ (where A¹⁶=oxygen, A¹⁷=sulfur and R⁴⁶,R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.152, in particular to the compounds of the formulae I.152.1 tol.152.689,.which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is oxygen and Q is Q⁷ (where A¹⁶=oxygen,A¹⁷=sulfur and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.153, in particular to the compounds of the formulae I.153.1 toI.153.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is sulfur and Q is Q⁷ (where A¹⁶=oxygen,A¹⁷=sulfur and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.154, in particular to the compounds of the formulae I.154.1 toI.154.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that B is a bond and Q is Q⁷ (where A¹⁶=oxygen,A¹⁷=sulfur and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.155, in particular to the compounds of the formulae I.155.1 toI.155.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Y is SO₂ and Q is Q⁷ (where A¹⁶=oxygen,A¹⁷=sulfur and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

Extraordinary preference is also given to the compounds of the formulaI.156, in particular to the compounds of the formulae I.156.1 to 1.156.689, which differ from the corresponding compounds of the formulaeI.1.1 to I.1.689 in that Y is SO₂NR² and Q is Q⁷ (where A¹⁶=oxygen,A¹⁷=sulfur and R⁴⁶, R⁴⁷ form a chain —CH₂—CH₂—O—CH₂—).

The benzenesulfonamide derivatives of the formula I can be obtained bydifferent routes, for example by one of the processes below:

Process A

Appropriately substituted aromatic compounds of the formula VIII are, bychlorosulfonylation, converted into the corresponding benzenesulfonylchlorides of the formula VII which are then reacted with ammonia to givethe corresponding sulfonamides of the formula V. The sulfonamides of theformula V are then reacted with (thio)phosgene of the formula VI to givethe benzenesulfonyl iso(thio)cyanates of the formula II which are thenreacted with amines of the formula III or alcohols or thiols of theformula IV to give the desired benzenesulfonamide derivatives of theformula I, where X³ is hydrogen, Y is —C(A)B and B is NR², oxygen orsulfur and the other radicals are as defined under claim 1:

Q in formula VIII denotes the radicals Q¹ to Q³⁹ mentioned above or asubstituent which is a precursor suitable for the synthesis of Q¹ toQ³⁹, for example a nitro or carboxyl group.

The chlorosulfonylation of the aromatic compounds of the formula VIII togive the corresponding benzenesulfonyl chlorides of the formula VII isusually carried out at temperatures of from 0° C. to 150° C., preferablyfrom 20° C. to 130° C., particularly preferably from 30° C. to 110° C.,using, for example, chlorosulfonic acid, sulfonyl chloride (SO₂Cl₂) orusing sulfonyl chloride in the presence of chlorosulfonic acid in aninert organic solvent [cf. Houben-Weyl, Methoden der organischen Chemie(Methods of organic chemistry), Vol. 9, 1955, pp. 572-579].

Suitable solvents are halogenated hydrocarbons, such as methylenechloride, chloroform and chlorobenzene, nitriles, such as acetonitrileand propionitrile, and also chlorosulfonic acid, particularly preferablychlorosulfonic acid.

It is also possible to use mixtures of the solvents mentioned.

If appropriate, this reaction can also be carried out in the presence ofa metal catalyst, for example aluminum chloride, analogously to aFriedel-Crafts reaction [cf. Houben-Weyl, Methoden der organischenChemie, Vol. 9, 1955, pp. 578-579].

Suitable acids and acid catalysts include inorganic acids, such ashydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acidand perchloric acid, Lewis acids, such as boron trifluoride, aluminumtrichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chlorideand zinc(II) chloride.

The acid catalysts are generally employed in catalytic amounts; however,they can also be used in equimolar amounts, in excess, or, ifappropriate, as solvent.

The starting materials are generally reacted with one another inequimolar amounts. It may be advantageous to use an excess ofchlorosulfonic acid or sulfonyl chloride, based on VIII, or to workdirectly in chlorosulfonic acid, as solvent.

The reaction mixtures are worked up in a customary manner, for exampleby mixing with water, phase separation and, if appropriate,chromatographic purification of the crude products. Some of theintermediates and end products are obtained in the form of viscous oilswhich can be freed from volatile components or purified under reducedpressure and at moderately elevated temperatures. If the intermediatesand end products are obtained as solids, purification can also becarried out by recrystallization or digestion.

Furthermore, it is also possible to cleave dialkyl sulfides withchlorine in the presence of water, followed by conversion into thecorresponding benzenesulfonyl chlorides of the formula VII [cf.Houben-Weyl, Methoden der organischen Chemie, Vol. 9, 1955, pp.580-582].

Analogously, it is also possible to convert thiophenols into thecorresponding benzenesulfonyl chlorides of the formula VII [cf.Houben-Weyl, Methoden der organischen Chemie, Vol. 9,1955, p. 582].

Benzenesulfonyl chlorides of the formula VII can also be prepared byreacting benzenesulfonic acids with chlorinating agents such as thionylchloride, phosgene, phosphorus trichloride or phosphorus pentachloride[cf. Houben-Weyl, Methoden der organischen Chemie, Vol. 9,1955,pp.564-568].

It is also possible to convert anilides via their diazonium salts withsulfur dioxide in the presence of copper(II) chloride (Meerweinreaction) into the corresponding benzenesulfonyl chlorides of theformula VII [cf. Houben-Weyl, Methoden der organischen Chemie, Vol.9,1955, p. 579-580].

The starting materials required for preparing the compounds I are knownfrom the literature [for example CAS 112, 157842; JP 01/168662] or canbe prepared in accordance with the literature cited.

Benzenesulfonyl chlorides of the formula VII in which Q is Q⁷ are known,for example, from WO 02/38562.

The preparation of benzenesulfonyl chlorides of the formula VII in whichQ is Q²¹ is described, for example, in U.S. Pat. No. 5,169,430.

Benzenesulfonyl chlorides of the formula VII in which Q is Q³² areknown, for example, from WO 96/15115.

The preparation of benzenesulfonyl chlorides of the formula VII in whichQ is Q³⁸ is described, for example, in WO 95/02580.

Benzenesulfonyl chlorides of the formula VII having other radicals Q canbe prepared analogously to the methods mentioned above (cf. for exampleJP 05/164386). Further precursors are described in Böger, Wakabayashi,Peroxidizing Herbicides, Springer Verlag 1999.

The subsequent reaction of the benzenesulfonyl chlorides of the formulaVII with gaseous or aqueous ammonia to give the correspondingsulfonamides of the formula V where

X³=hydrogen is usually carried out at temperatures of from −10° C. to50° C., preferably from 0° C. to 30° C., particularly preferably from 5°C. to 15° C., in an inert organic solvent, if appropriate in thepresence of a base [cf. U.S. Pat. No. 5,169,430; WO 95102580;Houben-Weyl, Methoden der organischen Chemie, Vol. 9, 1955, pp. 398-400and 605].

Ammonia is preferably used in an excess of from 200 to 230%; however, itis also possible to use an auxiliary base.

Suitable auxiliary bases are, in general, inorganic compounds, such asalkali metal and alkaline earth metal hydroxides, such as lithiumhydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide,alkali metal and alkaline earth metal oxides, such as lithium oxide,sodium oxide, calcium oxide and magnesium oxide, alkali metal andalkaline earth metal hydrides, such as lithium hydride, sodium hydride,potassium hydride and calcium hydride, alkali metal amides, such aslithium amide, sodium amide, and potassium amide, alkali metal andalkaline earth metal carbonates, such as lithium carbonate, potassiumcarbonate and calcium carbonate, and also alkali metal bicarbonates,such as sodium bicarbonate, organometallic compounds, in particularalkali metal alkyls, such as methyllithium, butyllithium andphenyllithium, alkylmagnesium halides, such as methylmagnesium chloride,and also alkali metal and alkaline earth metal alkoxides, such as sodiummethoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide,potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases,for example tertiary amines, such as trimethylamine, triethylamine,diisopropylethylamine and N-methylpiperidine, pyridine, substitutedpyridines, such as collidine, lutidine and 4-dimethylaminopyridine, andalso bicyclic amines.

The bases are generally employed in catalytic amounts; however, they canalso be employed in equimolar amounts, in excess or, if appropriate, assolvent.

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane,cyclohexane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons, suchas toluene, o-, m- and p-xylene, halogenated hydrocarbons such asmethylene chloride, 1,2-dichloroethane, chloroform and chlorobenzene,ethers, such as diethyl ether, diisopropyl ether, tert-butylmethylether, dioxane, anisole and tetrahydrofuran, nitriles, such asacetonitrile and propionitrile, ketones, such as acetone, methylethylketone, diethyl ketone and tert-butyl methyl ketone, and alsodimethylformamide and dimethylacetamide, particularly preferablydioxane, tetrahydrofuran, 1,2-dichloroethane, toluene or cyclohexane.

It is also possible to use mixtures of the solvents mentioned.

Work-up and isolation of the products can be carried out in a mannerknown per se.

Further sulfonamides of formula V can be prepared by analogous reactionof benzenesulfonyl chlorides of the formula VII with an amine H₂NX³.

Sulfonamides of the formula V, in which Q is Q⁷ are described, forexample, in WO 02/38562.

U.S. Pat. No. 5,169,430 and WO 95/02580 describe sulfonamides of theformula V in which Q is Q²¹ and Q²⁸, respectively.

The reaction of the sulfonamides of the formula V where X³=hydrogen with(thio)phosgene of the formula VI to give benzenesulfonyliso(thio)cyanates of the formula II is usually carried out attemperatures of from 50° C. to 110C., preferably from 60° C. to 90° C.,in an inert organic solvent, if appropriate in the presence of acatalyst [cf. Houben-Weyl, Methoden der organischen Chemie, Vol.11, 2,1985, p.1106; U.S. Pat. No. 4,379,769; DD 238 522].

Suitable catalysts are, for example, aliphatic isocyanates, such as, forexample, n-propyl isocyanate, isopropyl isocyanate or n-butylisocyanate.

The catalyst is generally employed in a substoichiometric amount of from5% to 15% per mole of sulfonamide of the formula V.

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane,cyclohexane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons, suchas toluene, o-, m- and p-xylene, halogenated hydrocarbons, such asmethylene chloride, chloroform and chlorobenzene, ethers, such asdiethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane,anisole and tetrahydrofuran, nitriles, such as acetonitrile andpropionitrile, ketones, such as acetone, methyl ethyl ketone, diethylketone and tert-butyl methyl ketone, particularly preferably toluene,1,2-dichloroethane or chlorobenzene.

It is also possible to use mixtures of the solvents mentioned.

The starting materials are generally reacted with one another inequimolar amounts. It may be advantageous to employ an excess of VI,based on V.

Work-up and isolation of the products can be carried out in a mannerknown per se.

The conversion of the sulfonamides of the formula V where X³=hydrogeninto benzenesulfonyl iso(thio)cyanates of the formula II can also becarried out using diphosgene [ClC(O)OCCl₃] or using carbon disulfide inphosgene.

Expediently, the sulfonamides of the formula V where X³=hydrogen canalso be initially pre-treated with thionyl chloride under reflux andthen be reacted with phosgene to give benzenesulfonyl iso(thio)cyanatesof the formula II (cf. DE 43 22 726).

Benzenesulfonyl iso(thio)cyanates of the formula II can also be preparedby reacting sulfonamides of the formula V where X³=hydrogen withchlorosulfonyl isocyanate (cf. DE 31 32 944).

Benzenesulfonyl iso(thio)cyanates of the II can furthermore be preparedin a manner known per se by reacting benzenesulfonyl chlorides of theformula VII with alkali metal isocyanates (cf. U.S. Pat. No. 4,546,179).

The reaction of benzenesulfonyl iso(thio)cyanates of the II with aprimary amine of the formula III or an alcohol or thiol of the formulaIV to give the desired benzenesulfonamide derivatives of the formula Iwhere X³=hydrogen, Y=—C(A)B and B=NR², oxygen or sulfur is usuallycarried out at temperatures of from 0° C. to 120° C., preferably from10° C. to 100° C., particularly preferably from 20° C. to 70° C., in aninert organic solvent [cf. EP 162 723].

The reaction can be carried out under atmospheric pressure or underelevated pressure (up to 50 bar), preferably from 1 to 5 bar,continuously or batchwise.

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane,cyclohexane and mixtures of C₅-C₈-alkanes; nitrated hydrocarbons, suchas nitromethane, nitroethane, nitrobenzene, o-, m-, p-chloronitrobenzeneand o-nitrotoluene; aromatic hydrocarbons, such as toluene, o-, m- andp-xylene; halogenated hydrocarbons, such as methylene chloride,1,2-dichloroethane, chloroform and chlorobenzene, ethers, such asdiethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane,anisole and tetrahydrofuran and also nitriles, such as acetonitrile andpropionitrile, particularly preferably tetrahydrofuran, dioxane and1,2-dichloroethane.

It is also possible to use mixtures of the solvents mentioned.

As catalyst, it is possible to add, before or during the reaction, abase, which accelerates the reaction and improves the quality of theproduct.

Suitable bases are, in general, organic bases, for example tertiaryamines, such as trimethylamine, triethylamine, diisopropylethylamine,tri(n-propyl)amine, N-methylpiperidine, pyridine, substituted pyridines,such as collidine, lutidine and 4-dimethylaminopyridine, and alsobicyclic amines. Particular preference is given to triethylamine or1,4-diazabicyclo[2.2.2]octane.

The bases are generally employed in catalytic amounts; however, they canalso be employed in equimolar amounts.

The benzenesulfonyl iso(thio)cyanates of the II are generally reacted inequimolar amounts with the primary amine of the formula III or thealcohol or thiol of the formula IV. It may be advantageous to employ anexcess of III or IV, based on II.

Work-up and isolation of the products can be carried out in a mannerknown per se.

Process B

Sulfonamides of the formula V are reacted with (thio)carbamates of theformula IX to give the desired benzenesulfonamide derivatives of theformula I, where Y is —C(A)B and B is NR² and the other radicals are asdefined under claim 1:

Z in formula IX denotes a C₁-C₆-alkyl or phenyl radical, where bothradicals for their part may be partially or fully halogenated and/or maycarry one to three radicals from the group consisting of nitro,C₁-C₄-alkyl, C₁-C₄-alkoxy and C₁-C₄-alkoxycarbonyl.

This reaction is usually carried out at temperatures of from 0° C. to120° C., preferably from 20° C. to 100° C., in an inert organic solvent[cf. EP 141 777 and EP 101 670].

The reaction can be carried out under atmospheric pressure or underelevated pressure (up to 50 bar), preferably at 1 to 5 bar, continuouslyor batchwise.

Suitable solvents are aliphatic or cycloaliphatic hydrocarbons, such aspentane, 1,2,4-trimethylpentane, 2,2,3-trimethylpentane,2,3,3-trimethylpentane, hexane, heptane, octane, nonane, mixtures ofC₅-C₈-alkanes, pinane, cyclohexane, methylcyclohexane, o-, m-, p-cymene,petroleum fractions within a boiling point range of from 70° C. to 190°C., decalin, petroleum ether, ligroin; nitrated hydrocarbons, such asnitromethane, nitroethane, nitrobenzene, o-, m-, p-chloronitrobenzeneand o-nitrotoluene; aromatic hydrocarbons, such as toluene, o-, m- andp-xylene, halogenated hydrocarbons, such as 1,2-dichloroethane,1,1-dichloroethane, 1,2-cis-dichloroethylene, 1,1,1- or1,1,2-trichloroethane, trichloroethylene, tetrachloroethylene, 1,1,2,2-or 1,1,1,2-tetrachloroethane, pentachloroethane, dichloropropane,methylene chloride, dichlorobutane, chloroform, carbon tetrachloride,fluorobenzene, chlorobenzene, bromobenzene, iodobenzene, o-, m-,p-difluorobenzene, o-, m-, p-dichlorobenzene, o-, m-, p-dibromobenzene,o-, m-, p-chlorotoluene, 1,2,4-trichlorobenzene, chloronaphthalene,dichloronaphthalene; ethers, such as diethyl ether, ethyl propyl ether,diisopropyl ether, tert-butyl methyl ether, n-butyl ethyl ether,di-n-butyl ether, diisobutyl ether, diisoamyl ether, dioxane, cyclohexylmethyl ether, ethylene glycol dimethyl ether, β,β′-dichlorodiethylether, tetrahydrofuran, anisole, thioanisole, phenetol; nitriles, suchas acetonitrile, propionitrile, butyronitrile, isobutyronitrile,benzonitrile, m-chlorobenzonitrile; ketones, such as acetone, methylethyl ketone, diethyl ketone and tert-butyl methyl ketone; esters, suchas ethyl acetate, isobutyl acetate; amides, such as formamide,methylformamide, dimethylformamide; particularly preferably1,2dichloroethane, tetrahydrofuran, tert-butyl methyl ether and toluene.

It is also possible to use mixtures of the solvents mentioned.

As catalyst, a base can be added before or during the reaction, whichaccelerates the reaction and improves the quality of the product.

Suitable bases are, in general, organic bases, for example tertiaryamines, such as trimethylamine, triethylamine, diisopropylethylamine,tri(n-propyl)amine, N-methylpiperidine, pyridine, substituted pyridines,such as collidine, lutidine and 4-dimethylaminopyridine, and alsobicyclic amines. Particular preference is given to triethylamine and1,4-diazabicyclo[2.2.2]octane.

The bases are generally employed in catalytic amounts; however, they canalso be employed in equimolar amounts.

The sulfonamides of the formula V are generally reacted in equimolaramounts with the (thio)carbamate of the formula IX. It may beadvantageous to employ an excess of IX, based on V.

The work-up and isolation of the products can be carried out in a mannerknown per se.

By analogous reaction with carboxylic acid derivatives ZO(A)R¹, it ispossible to prepare benzenesulfonamide derivatives of the formula Iwhere Y=—C(A)B and B=a bond.

Process C

Sulfonamides of the formula V can be reacted with iso(thio)cyanates ofthe formula X to give the desired benzenesulfonamide derivatives of theformula I where Y is —C(A)B and B is NH and the other radicals are asdefined under claim 1:

This reaction is usually carried out at temperatures of from 0° C. to150° C., preferably from 10° C. to 100° C., in an inert organic solvent[cf. EP 234 352].

The reaction can be carried out under atmospheric pressure or underelevated pressure (up to 50 bar), preferably at 1 to 5 bar, continuouslyor batchwise.

Suitable solvents are aliphatic or cycloaliphatic hydrocarbons, such aspentane, 1,2,4-trimethylpentane, 2,2,3-trimethylpentane,2,3,3-trimethylpentane, hexane, heptane, octane, nonane, mixtures ofC₅-C₈-alkanes, pinane, cyclohexane, methylcyclohexane, o-, m-, p-cymene,petroleum fractions within a boiling point range of from 70° C. to 190°C., decalin, petroleum ether, ligroin; nitrated hydrocarbons, such asnitromethane, nitroethane, nitrobenzene, o-, m-, p-chloronitrobenzeneand o-nitrotoluene; aromatic hydrocarbons, such as toluene, o-, m- andp-xylene, halogenated hydrocarbons, such as 1,2-dichloroethane,1,1-dichloroethane, 1,2-cis-dichloroethylene, 1,1,1- or1,1,2-trichloroethane, trichloroethylene, tetrachloroethylene, 1,1,2,2-or 1,1,1,2-tetrachloroethane, pentachloroethane, dichloropropane,methylene chloride, dichlorobutane, chloroform, carbon tetrachloride,fluorobenzene, chlorobenzene, bromobenzene, iodobenzene, o-, m-,p-difluorobenzene, o-, m-, p-dichlorobenzene, o-, m-, p-dibromobenzene,o-, m-, p-chlorotoluene, 1,2,4-trichlorobenzene, chloronaphthalene,dichloronaphthalene; ethers, such as diethyl ether, ethyl propyl ether,diisopropyl ether, tert-butyl methyl ether, n-butyl ethyl ether,di-n-butyl ether, diisobutyl ether, diisoamyl ether, dioxane, cyclohexylmethyl ether, ethylene glycol dimethyl ether, β,β′-dichlorodiethylether, tetrahydrofuran, anisole, thioanisole, phenetol; nitriles, suchas acetonitrile, propionitrile, butyronitrile, isobutyronitrile,benzonitrile, m-chlorobenzonitrile; ketones, such as acetone, methylethyl ketone, diethyl ketone and tert-butyl methyl ketone; esters, suchas ethyl acetate, isobutyl acetate; amides, such as formamide,methylformamide, dimethylformamide; particularly preferably1,2-dichloroethane, tetrahydrofuran, ethyl acetate, tert-butyl methylether, acetone and also toluene.

It is also possible to use mixtures of the solvents mentioned.

As catalyst, a base can be added before or during-the reaction, whichaccelerates the reaction and improves the quality of the product.

Suitable bases are, in general, organic bases, for example tertiaryamines, such as trimethylamine, triethylamine, diisopropylethylamine,tri(n-propyl)amine, N-methylpiperidine, pyridine, substituted pyridines,such as collidine, lutidine and 4-dimethylaminopyridine, and alsobicyclic amines. Particular preference is given to triethylamine or2,4,6-collidine.

The bases are generally employed in catalytic amounts; however, they canalso be employed in equimolar amounts.

The sulfonamides of the formula V are generally reacted in equimolaramounts with an iso(thio)cyanate of the formula X. It may beadvantageous to employ an excess of X, based on V.

To bring the reaction to completion, the reaction mixture may, afteraddition of the components, be stirred at from 0 to 120° C., preferablyfrom 10 to 100° C., in particular from 20 to 80° C., for another 20 min.to 24 h.

Work-up and isolation of the products can be carried out in a mannerknown per se.

Process D

Sulfonamides of the formula V can be reacted with halides of the formulaXI to give the desired benzenesulfonamide derivatives of the formula I:

Hal in formula XI denotes halogen, such as fluorine, chlorine, bromine,particularly preferably chlorine.

This reaction is usually carried out at temperatures of from 0° C. to150° C., preferably from 10° C. to 100° C., in an inert organic solvent[cf. JP 05/194386, CAS 120, 134277].

The reaction can be carried out under atmospheric pressure or underelevated pressure (up to 50 bar), preferably at 1 to 5 bar, continuouslyor batchwise.

Suitable solvents are aliphatic or cycloaliphatic hydrocarbons, such aspentane, 1,2,4-trimethylpentane, 2,2,3-trimethylpentane,2,3,3-trimethylpentane, hexane, heptane, octane, nonane, mixtures ofC₅-C₈-alkanes, pinane, cyclohexane, methylcyclohexane, o-, m-, p-cymene,petroleum fractions within a boiling point range of from 70° C. to 190°C., decalin, petroleum ether, ligroin; nitrated hydrocarbons, such asnitromethane, nitroethane, nitrobenzene, o-, m-, p-chloronitrobenzeneand o-nitrotoluene; aromatic hydrocarbons, such as toluene, o-, m- andp-xylene, halogenated hydrocarbons, such as 1,2-dichloroethane,1,1-dichloroethane, 1,2-cis-dichloroethylene, 1,1,1- or1,1,2-trichloroethane, trichloroethylene, tetrachloroethylene, 1,1,2,2-or 1,1,1,2-tetrachloroethane, pentachloroethane, dichloropropane,methylene chloride, dichlorobutane, chloroform, carbon tetrachloride,fluorobenzene, chlorobenzene, bromobenzene, iodobenzene, o-, m-,p-difluorobenzene, o-, m-, p-dichlorobenzene, o-, m-, p-dibromobenzene,o-, m-, p-chlorotoluene, 1,2,4-trichlorobenzene, chloronaphthalene,dichloronaphthalene; ethers, such as diethyl ether, ethyl propyl ether,diisopropyl ether, tert-butyl methyl ether, n-butyl ethyl ether,di-n-butyl ether, diisobutyl ether, diisoamyl ether, dioxane, cyclohexylmethyl ether, ethylene glycol dimethyl ether, β,β′-dichlorodiethylether, tetrahydrofuran, anisole, thioanisole, phenetol; nitriles, suchas acetonitrile, propionitrile, butyronitrile, isobutyronitrile,benzonitrile, m-chlorobenzonitrile; ketones, such as acetone, methylethyl ketone, diethyl ketone and tert-butyl methyl ketone; esters, suchas ethyl acetate, isobutyl acetate; amides, such as formamide,methylformamide, dimethylformamide; particularly preferably1,2-dichloroethane, tetrahydrofuran, ethyl acetate, acetonitrile andalso toluene.

It is also possible to use mixtures of the solvents mentioned.

As catalyst, a base can be added before or during the reaction, whichaccelerates the reaction and improves the quality of the product.

Suitable bases are, in general, inorganic compounds, such as alkalimetal and alkaline earth metal hydroxides, such as lithium hydroxide,sodium hydroxide, potassium hydroxide and calcium hydroxide, alkalimetal and alkaline earth metal carbonates, such as lithium carbonate,potassium carbonate and calcium carbonate, and also alkali metalbicarbonates, such as sodium bicarbonate, moreover organic bases, forexample tertiary amines, such as trimethylamine, triethylamine,diisopropylethylamine, tri(n-propyl)amine, N-methylpiperidine, pyridine,substituted pyridines, such as collidine, lutidine and4-dimethylaminopyridine, and also bicyclic amines. Particular preferenceis given to triethylamine or 2,4,6-collidine.

The bases are generally employed in catalytic amounts; however, they canalso be employed in equimolar amounts.

The sulfonamides of the formula V are generally reacted in equimolaramounts with the isocyanate or isothiocyanate of the formula X. It maybe advantageous to employ an excess of XI, based on V.

To bring the reaction to completion, the reaction mixture may, afteraddition of the components, be stirred at from 0 to 120° C., preferablyfrom 10 to 100° C., in particular from 20 to 80° C., for another 20 minto 24 h.

Work-up and isolation of the products can be carried out in a mannerknown per se.

Analogously to process D described above, it is also possible to reactsulfonamides of the formula V with anhydrides of the formula XIIA[C(=A)−R¹]₂   XIIto give the desired benzenesulfonamide derivatives of the formula I inwhich Y is —C(A)B where B is a bond and the other radicals are asdefined under claim 1.

Process E

Sulfonyl(thio)carbamates of the formula XIII are reacted with amines ofthe formula XIV to give the desired benzenesulfonamide derivatives ofthe formula I where Y is —C(A)B and B is NR² and the other radicals areas defined under claim 1:

Z in formula XIII is C₁-C₆-alkyl or phenyl, where both radicals may fortheir part be partially or fully halogenated and/or may carry one tothree radicals from the group consisting of nitro, C₁-C₄-alkyl,C₁-C₄-alkoxy and C₁-C₄-alkoxycarbonyl.

This reaction is usually carried out at temperatures of from 0° C. to120° C., preferably from 10° C. to 100° C., in an inert organic solvent[cf. EP 120 814; EP 101 407].

Suitable solvents are aliphatic or cycloaliphatic hydrocarbons, such aspentane, 1,2,4-trimethylpentane, 2,2,3-trimethylpentane,2,3,3-trimethylpentane, hexane, heptane, octane, nonane, mixtures ofC₅-C₈-alkanes, pinane, cyclohexane, methylcyclohexane, o-, m-, p-cymene,petroleum fractions within a boiling point range of from 70° C. to 190°C., decalin, petroleum ether, ligroin; nitrated hydrocarbons, such asnitromethane, nitroethane, nitrobenzene, o-, m-, p-chloronitrobenzeneand o-nitrotoluene; aromatic hydrocarbons, such as toluene, o-, m- andp-xylene, halogenated hydrocarbons, such as 1,2-dichloroethane,1,1-dichloroethane, 1,2-cis-dichloroethylene, 1,1,1- or1,1,2-trichloroethane, trichloroethylene, tetrachloroethylene, 1,1,2,2-or 1,1,1,2-tetrachloroethane, pentachloroethane, dichloropropane,methylene chloride, dichlorobutane, chloroform, carbon tetrachloride,fluorobenzene, chlorobenzene, bromobenzene, iodobenzene, o-, m-,p-difluorobenzene, o-, m-, p-dichlorobenzene, o-, m-, p-dibromobenzene,o-, m-, p-chlorotoluene, 1,2,4-trichlorobenzene, chloronaphthalene,dichloronaphthalene; ethers, such as diethyl ether, ethyl propyl ether,diisopropyl ether, tert-butyl methyl ether, n-butyl ethyl ether,di-n-butyl ether, diisobutyl ether, diisoamyl ether, dioxane, cyclohexylmethyl ether, ethylene glycol dimethyl ether, β,β′-dichlorodiethylether, tetrahydrofuran, anisole, thioanisole, phenetol; nitriles, suchas acetonitrile, propionitrile, butyronitrile, isobutyronitrile,benzonitrile, m-chlorobenzonitrile; ketones, such as acetone, methylethyl ketone, diethyl ketone and tert-butyl methyl ketone; esters, suchas ethyl acetate, isobutyl acetate; amides, such as formamide,methylformamide, dimethylformamide; particularly preferablytetrahydrofuran, dioxane, dimethylformamide and also toluene.

It is also possible to use mixtures of the solvents mentioned.

As catalyst, a base can be added before or during the reaction, whichaccelerates the reaction and improves the quality of the product.

Suitable bases are, in general, organic bases, for example tertiaryamines, such as trimethylamine, triethylamine, diisopropylethylamine,tri(n-propyl)amine, N-methylpiperidine, pyridine, substituted pyridines,such as collidine, lutidine and 4-dimethylaminopyridine, and alsobicyclic amines. Particular preference is given to triethylamine and1,4-diazabicyclo[2.2.2]octane.

The bases are generally employed in catalytic amounts; however, they canalso be employed in equimolar amounts.

The sulfonylcarbamates of the formula XII are generally reacted inequimolar amounts with an amine of the formula XIV. It may beadvantageous to employ an excess of XIV, based on XII.

Work-up and isolation of the products can be carried out in a mannerknown per se.

The starting materials required for preparing the compounds I are knownfrom the literature [cf. for example, CAS 112,157842; JP 01/168662], orthey can be prepared in accordance with the literature cited.

Process F

Compounds of the formula I in which the radicals Q carry thesubstituents R³, R⁴, R⁷, R¹¹, R¹⁸, R¹⁹, R²⁴, R²⁷, R²⁹, R³², R³⁹, R⁴⁴-R⁴⁷on their nitrogen atoms [these radicals denoting, inter alia,C₁-C₆-alkyl or amino, C₁-C₆-alkylamino or di(C₁-C₆-alkyl)amino] can beprepared by reacting, either prior to the synthesis of the sulfonamideside chain (i.e. at the stage of the aromatic compounds of the formulaVIII) or after synthesis of the sulfonamide side chain, with an alkylhalide, alkyl sulfate, alkyl tosylate or an electrophilic aminatingagent of the formula XVII, analogously to the methods described in theliterature.

Examples of electrophilic aminating agents of the formula XVII are2,4-dinitrophenylhydroxylamine and o-mesitylenesulfonyl hydroxylamine.

The benzenesulfonyl chlorides of the formula VII mentioned above can beconverted, for example, by action of alcohols, expediently in thepresence of a base, into the corresponding benzenesulfonyl esters[Houben-Weyl, Methoden der organischen Synthese, Vol. 9, 1955, p. 663].The benzenesulfonyl esters can then be alkylated or aminated on the freenitrogen atoms of the corresponding radicals Q. Subsequently, thebenzenesulfonyl esters can be hydrolyzed again [cf. Kocienski,Protecting groups, Thieme-Verlag 1994; Greene, Wuts, Protecting groupsin organic synthesis, Wiley 1999; Houben-Weyl, Methoden der organischenChemie, Vol. E5 part 1, 1985, p. 223f.).

By way of example, an amination at the radical Q=Q²¹ is shown here. Theaminations of the other radicals Q and alkylations at the radicals Q canbe carried out analogously. This route affords, for example, sulfonicacids of the formula XVI. These can then be converted using methodsknown from the literature into the desired benzenesulfonamidederivatives of the formula I.

This reaction is usually carried out at temperatures of from 10° C. to80° C., preferably from 20° C. to 40° C., in an inert organic solvent inthe presence of a base [cf. DE 19 652 431; WO 01/83459].

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane,cyclohexane and mixtures of C₅-C₈-alkanes, aromatic hydrocarbons, suchas toluene, o-, m- and p-xylene, halogenated hydrocarbons, such asmethylene chloride, chloroform and chlorobenzene, ethers, such asdiethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane,anisole and tetrahydrofuran, nitriles, such as acetonitrile andpropionitrile, ketones, such as acetone, methyl ethyl ketone, diethylketone and tert-butyl methyl ketone, and also dimethyl sulfoxide,dimethyl formamide and dimethylacetamide, particularly preferablytetrahydrofuran, dioxane, acetonitrile and also dimethylformamide.

It is also possible to use mixtures of the solvents mentioned.

Suitable bases are, in general, inorganic compounds, for example alkalimetal and alkaline earth metal hydroxides, such as lithium hydroxide,sodium hydroxide, potassium hydroxide and calcium hydroxide, alkalimetal and alkaline earth metal oxides, such as lithium oxide, sodiumoxide, calcium oxide and magnesium oxide, alkali metal and alkalineearth metal hydrides, such as lithium hydride, sodium hydride, potassiumhydride and calcium hydride, alkali metal and alkaline earth metalcarbonates, such as lithium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal bicarbonates, such as sodiumbicarbonate, alkali metal and alkaline earth metal alkoxides, such assodium methoxide, sodium ethoxide, potassium ethoxide, potassiumtert-butoxide, potassium tert-pentoxide and dimethoxymagnesium, moreoverorganic bases, for example tertiary amines, such as trimethylamine,triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine,substituted pyridines, such as collidine, lutidine and4-dimethylaminopyridine, and also bicyclic amines. Particular preferenceis given to potassium carbonate and also calcium carbonate.

The bases are generally employed in catalytic amounts; however, they canalso be employed in equimolar amounts, in excess or, if appropriate, assolvent.

The starting materials are generally reacted with one another inequimolar amounts. However, it may also be advantageous to employ anexcess of XVII, based on XV.

Work-up and isolation of the products can be carried out in a mannerknown per se.

The starting materials required for preparing the compounds I are knownfrom the literature [for example CAS 112, 157842; JP 01168662], or theycan be prepared in accordance with the literature cited.

The present invention also provides benzenesulfonyl iso(thio)cyanates ofthe formula II

where X¹, X², A and Q are as defined under claim 1.

The particularly preferred embodiments of the intermediates with respectto the variables correspond to those of the radicals X¹, X², A and Q offormula I.

Particular preference is given to intermediates of the formula IV inwhich

-   -   X¹ is hydrogen, fluorine or chlorine;        -   particularly preferably hydrogen or fluorine;        -   especially preferably fluorine;    -   X² is hydrogen, cyano, CS—NH₂ or halogen;        -   particularly preferably hydrogen, halogen such as fluorine            and chlorine;        -   especially preferably chlorine; and    -   Q is Q¹, Q², Q⁵, Q⁷, Q⁸, Q¹⁰, Q¹², Q¹³, Q¹⁷, Q²⁰, Q²¹, Q²², Q²³,        Q²⁴, Q²⁷, Q³¹, Q³², Q³⁴, Q³⁸ or Q³⁹,        -   particularly preferably Q¹, Q², Q⁵, Q⁷, Q⁸, Q¹⁰, Q¹², Q¹³,            Q¹⁷, Q²⁰, Q²¹, Q²², Q²⁴, Q²⁷, Q³¹, Q³², Q³⁸ or Q³⁹,        -   especially preferably Q⁵, Q⁷, Q²¹, Q²², Q²⁷, Q³², Q³⁸ or            Q³⁹,        -   with extraordinary preference Q⁷, Q²¹, Q²², Q²⁷, Q³², Q³⁸ or            Q³⁹,        -   with most extraordinary preference Q²¹, Q³² or Q³⁸.

PREPARATION EXAMPLES EXAMPLE 12-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]-benzenesulfonamide

With stirring, 1.6 g (93.8 mmol) of ammonia gas were, at 0° C.,introduced into a mixture of 18 g (44.6 mmol) of2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]-benzenesulfonylchloridein tetrahydrofuran (THF). Then, at 10° C., ethyl acetate was added andthe mixture was acidified with 1N hydrochloric acid. The phases wereseparated and the aqueous phase was extracted, and the combined organicphases were then washed, dried and the solvent was removed. Customarypurification methods gave 14.4 g (82.4% of theory) of the title compound(m.p.: 257-258° C.).

EXAMPLE 22-Chloro4-fluoro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]benzenesulfonylisocyanate

At 60° C., 7.4 g (62.3 mmol) of thionyl chloride were added dropwisewith stirring to a suspension of 10.0 g (24.9 mmol) of2-chloro-4-fluoro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]-benzenesulfonylamidein 1,2-dichloroethane. The mixture was then boiled under reflux for 4 h.The mixture was then cooled to 60° C., a catalytic amount of pyridinewas added and phosgene was introduced under reflux for 12 h until aclear solution was obtained. After cooling to 30° C., the product wasfreed from the solvent. This gave 11.6 g (98% of theory) of the titlecompound.

¹H-NMR (400 MHz, CDCl₃) δ [ppm]=8.12 (d, 1H), 7.55 (d, 1H), 6.38 (s,1H), 3.57 (s, 3H).

EXAMPLE 32-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]-benzenesulfonylisocyanate

10.0 g (26.1 mmol) of2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]-benzenesulfonamidewere reacted analogously to the method described in Example 2. This gave13.4 g (99% of theory) of the title compound.

¹H-NMR (400 MHz, CDCl₃) δ [ppm]=8.02 (s, 1H), 7.76 (d, 2H), 7.5 (d, 1H),6.38 (s, 1H), 3.70 (s, 3H).

EXAMPLE 4 (No. 3.32)Benzyl{2-chloro-4-fluoro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]phenyl}sulfonylcarbamate

With stirring, 0.6 g (1.4 mmol) of2-chloro-4-fluoro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]benzenesulfonylisocyanate in 1,2-dichloroethane was added to a solutionof 0.15 g (1.4 mmol) of benzyl alcohol in methylene chloride, and thereaction mixture was stirred overnight. Removal of the solvent andcustomary purification methods gave 0.4 g (52% of theory) of the titlecompound as a colorless solid (m.p.: 231-232 ° C.).

EXAMPLE 5 (No. 2.26)3-[4-Chloro-2-fluoro-5-{[isopropyl(methyl)amino]carbonylaminosulfonyl}phenyl]-1-methyl-2,4-dioxo-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine

With stirring, 1.0 g (2.34 mmol) of2-chloro-4-fluoro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]benzenesulfonylisocyanate in 1,2-dichloroethane was added to a solution of 0.34 g (4.68mmol) of N-methylisopropylamine in 1,2-dichloroethane, and the mixturewas stirred overnight. The reaction mixture was concentrated, theresidue was taken up in methylene chloride and 0.5N hydrochloric acidwas added. The organic phase was then dried and the solvent was removed.This gave 0.5 g (42% of theory) of the title compound as a colorlesssolid (m.p.: 145° C.).

EXAMPLE 6 (No. 4.5)N-isobutynyl-[2-chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1-(2H)-pyrimidinyl)]benzenesulfonamide

With stirring, 0.15 g (1.43 mmol) of isobutyryl chloride was added to amixture of 0.5 g (1.3 mmol) of2-chloro-4-fluoro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-(2H)-pyrimidin-1-yl]benzenesulfonylisocyanate, 0.26 g (2.61 mmol) of triethylamine and catalytic amounts ofN,N-dimethylaminopyridine in methylene chloride, and the mixture wasstirred overnight. The reaction mixture was washed with 1N hydrochloricacid and dried and the solvent was removed. This gives 0.6 g (96% oftheory) of the title compound as a colorless solid (m.p.: 114-116 ° C.).

In addition to the compounds above, Tables 2 to 4 list furtherbenzenesulfonamide derivatives of the formula I which were prepared orare preparable in a manner similar to the processes described above.TABLE 2 2

No. X¹ X² R¹ R² R²⁹ m.p. [° C.] 2.1 H Cl CH₃ H CH₃ 2.2 H Cl CH₃ H NH₂2.3 H Cl CH₃ CH₃ CH₃ 2.4 H Cl CH₃ CH₃ NH₂ 2.5 H Cl OCH₃ CH₃ CH₃  95 2.6H Cl C₂H₅ H CH₃ 2.7 H Cl C₂H₅ H NH₂ 2.8 H Cl C₂H₅ C₂H₅ CH₃ 2.9 H ClCH₂CH₂CH₃ H CH₃ 2.10 H Cl CH₂CH₂CH₃ H NH₂ 2.11 H Cl CH(CH₃)₂ H CH₃ 2.12H Cl CH(CH₃)₂ CH₃ CH₃ 197 2.13 H Cl CH₂═CH—CH₂ H CH₃ 2.14 H Cl4-methoxy-6-methyl- H CH₃ 209-211 pyrimidin-2-yl 2.15 H Cl4,6-dimethoxy- H CH₃ 208-212 pyrimidin-2-yl 2.16 H Cl4-methoxy-6-methyl- H CH₃ 146-175 1,3,5-triazin-2- yl 2.17 F Cl CH₃ HCH₃ 228-230 2.18 F Cl CH₃ H NH₂ 2.19 F Cl CH₃ CH₃ CH₃ 198-205 2.20 F ClCH₃ CH₃ NH₂ 2.21 F Cl C₂H₅ H CH₃ 2.22 F Cl C₂H₅ H NH₂ 2.23 F Cl C₂H₅ CH₃CH₃ 2.24 F Cl CH₂CH₂CH₃ H CH₃ 2.25 F Cl CH₂CH₂CH₃ CH₃ CH₃ 2.26 F ClCH(CH₃)₂ CH₃ CH₃ 145 (decomposition) 2.27 F Cl CH(CH₃)₂ CH(CH₃)₂ CH₃179-181 2.28 F Cl CH(CH₃)C≡CH CH₃ CH₃ 160-165 2.29 F Cl C₆H₅ H CH₃ 1602.30 F Cl —(CH₂)₅— CH₃ 2.31 F Cl —(CH₂)₆— CH₃ 2.32 Cl Cl CH₃ H CH₃234-235 2.33 Cl Cl CH₃ CH₃ CH₃ 2.34 Cl Cl CH₃ CH₃ NH₂ 2.35 Cl Cl C₂H₅ HCH₃ 2.36 Cl Cl CH₂CH₂CH₃ H CH₃ 2.37 F Cl CH(CH₃)₂ H NH₂

TABLE 3 3

No. X¹ X² A B R¹ R²⁹ m.p. [° C.] 3.1 H Cl O O CH₃ CH₃ 120-148 3.2 H Cl OO C₂H₅ CH₃ 189-190 3.3 H Cl O O CH₂CH₂CH₃ CH₃ 3.4 H Cl O O CH(CH₃)₂ CH₃3.5 H Cl O O (CH₂)₃CH₃ CH₃ 194-195 3.6 H Cl O O CH(CH₃)CH₂CH₃ CH₃ 3.7 HCl O O CH₂CH(CH₃)₂ CH₃ 3.8 H Cl O O C(CH₃)₃ CH₃ 3.9 H Cl O O (CH₂)₄CH₃CH₃ 3.10 H Cl O O cyclopentyl CH₃ 114-116 3.11 H Cl O O CH₂CH₂Cl CH₃3.12 H Cl O O (CH₂)OCH₃ CH₃ 3.13 H Cl O O (CH₂)SCH₃ CH₃ 3.14 H Cl O OCH₂CH₂CN CH₃ 3.15 H Cl O S CH₃ CH₃ 3.16 H Cl O S C₂H₅ CH₃ 3.17 H Cl O SCH₂CH₂CH₃ CH₃ 3.18 F Cl O O CH₃ CH₃ 120-135 3.19 F Cl O O C₂H₅ CH₃228-231 3.20 F Cl O O CH₂CH₂CH₃ CH₃ 203 3.21 F Cl O O CH(CH₃)₂ CH₃228-230 3.22 F Cl O O (CH₂)₃CH₃ CH₃ 238 3.23 F Cl O O CH(CH₃)CH₂CH₃ CH₃195-198 3.24 F Cl O O CH₂CH(CH₃)₂ CH₃ 233-235 3.25 F Cl O O C(CH₃)₃ CH₃185 3.26 F Cl O O (CH₂)₄CH₃ CH₃ 235 3.27 F Cl O O cyclopentyl CH₃ 2143.28 F Cl O O CH₂CH₂Cl CH₃ 3.29 F Cl O O (CH₂)OCH₃ CH₃ 3.30 F Cl O O(CH₂)SCH₃ CH₃ 3.31 F Cl O O CH₂CH₂CN CH₃ 3.32 F Cl O O CH₂C₆H₅ CH₃231-232 3.33 F Cl O S CH₃ CH₃ 3.34 F Cl O S C₂H₅ CH₃ 3.35 F Cl O SCH₂CH₂CH₃ CH₃ 3.36 Cl Cl O S CH₃ CH₃ 3.37 Cl Cl O S C₂H₅ CH₃ 3.38 Cl ClO S CH₂CH₂CH₃ CH₃ 3.39 Cl Cl O O CH₃ CH₃ 218-220 3.40 Cl Cl O O C₂H₅ CH₃235-237 3.41 F Cl O O CH₂COOCH₃ CH₃ 142-160 3.42 F Cl O O C(CH₃)₂CH₂OCH₃CH₃ 178

TABLE 4 4

No. X¹ X² R¹ R²⁹ m.p. [° C.] 4.1 H Cl H CH₃ 4.2 H Cl CH₃ CH₃ 4.3 H ClC₂H₅ CH₃ 4.4 H Cl CH₂CH₂CH₃ CH₃ 4.5 H Cl CH(CH₃)₂ CH₃ 114-116 4.6 H Cl(CH₂)₃CH₃ CH₃ 4.7 H Cl CH(CH₃)CH₂CH₃ CH₃ 4.8 H Cl CH₂CH(CH₃)₂ CH₃ 4.9 HCl cyclopentyl CH₃ 4.10 H Cl CH₃ NH₂ 4.11 H Cl C₂H₅ NH₂ 4.12 H ClCH₂CH₂CH₃ NH₂ 4.13 F Cl CH₃ CH₃ 269 (decomposition) 4.14 F Cl C₂H₅ CH₃229-230 4.15 F Cl CH₂CH₂CH₃ CH₃ 4.16 F Cl CH(CH₃)₂ CH₃ 243-245 4.17 F ClCH₂Cl CH₃ 4.18 F Cl CF₃ CH₃ 4.19 F Cl C₆H₅ CH₃ 4.20 F Cl 2-Cl—C₆H₄ CH₃4.21 F Cl 3-Cl—C₆H₄ CH₃ 4.22 F Cl 4-Cl—C₆H₄ CH₃ 4.23 F ClCH₂(4-CH₃—C₆H₄) CH₃ 4.24 Cl Cl CH₃ CH₃ 275-277 4.25 Cl Cl C₂H₅ CH₃225-230 4.26 Cl Cl CH₂CH₂CH₃ CH₃ 4.27 Cl Cl CH₂CH(CH₃)₂ CH₃ 4.28 Cl ClCH₃ NH₂ 4.29 Cl Cl C₂H₅ NH₂ 4.30 Cl Cl CH₂CH₂CH₃ NH₂

Biological Activity

The benzenesulfonamide derivatives of the formula I and theiragriculturally useful salts are suitable, both in the form of isomermixtures and in the form of the pure isomers, as herbicides. Theherbicidal compositions comprising compounds of the formula I controlvegetation on non-crop areas very efficiently, especially at high ratesof application. They act against broad-leaved weeds and harmful grassesin crops such as wheat, rice, maize, soya and cotton without causing anysignificant damage to the crop plants. This effect is mainly observed atlow rates of application.

Depending on the application method used, the compounds of the formulaI, or the herbicidal compositions comprising them, can additionally beemployed in a further number of crop plants for eliminating undesirableplants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napusvar. napus, Brassica napus var. napobrassica, Brassica rapa var.silvestris, Camellia sinensis, Carthamus tinctorius, Caryaillinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffeacanephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucuscarota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypiumhirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypiumvitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare,Humulus lupulus, lpomoea batatas, Juglans regia, Lens culinaris, Linumusitatissimum, Lycopersicon lycopersicum, Malus spec., Manihotesculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica),Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris,Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica,Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharumofficinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s.vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum,Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds of the formula I may also be used in cropswhich tolerate the action of herbicides owing to breeding, includinggenetic engineering methods.

Furthermore, the benzenesulfonamide derivatives of the formula I andtheir agriculturally useful salts are also suitable for the desiccationand/or defoliation of plants.

As desiccants, they are particularly suitable for desiccating theabove-ground parts of crop plants such as potatoes; oilseed rape,sunflowers and soybeans. This allows completely mechanical harvesting ofthese important crop plants.

Also of economic interest is

-   -   the concentrated, within a certain time, fruit drop or the        reduction of the adherence of the fruits to the plant, for        example in the case of citrus fruit, olives or other species and        varieties of pomaceous fruit, stone fruit and hard-shelled        fruit, thus facilitating the harvesting of these fruits, and        also    -   the controlled defoliation of useful plants, in particular        cotton.

The drop, promoted by using compounds of the formula I according to theinvention and agriculturally useful salts thereof, is a result of theformation of abscission tissue between fruits or leaves and the shoot ofthe plants.

The defoliation of cotton is of very particular economic interest, sinceit facilitates harvesting. At the same time, the reduced period of timewithin which the individual plants mature results in a better quality ofthe harvested fiber material.

The compounds of the formula I, or the herbicidal compositionscomprising them, can be used for example in the form of ready-to-sprayaqueous solutions, powders, suspensions, also highly-concentratedaqueous, oily or other suspensions or dispersions, emulsions, oildispersions, pastes, dusts, materials for broadcasting or granules, bymeans of spraying, atomizing, dusting, broadcasting or watering. The useforms depend on the intended aims; in any case, they should ensure avery fine distribution of the active compounds according to theinvention.

The herbicidal compositions comprise a herbicidally effective amount ofat least one compound of the formula I or an agriculturally useful saltof I and auxiliaries customary for formulating crop protection agents.

Essentially, suitable inert auxiliaries include:

mineral oil fractions of medium to high boiling point, such as keroseneand diesel oil, furthermore coal tar oils and oils of vegetable oranimal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g.paraffins, tetrahydronaphthalene, alkylated naphthalenes and theirderivatives, alkylated benzenes and their derivatives, alcohols such asmethanol, ethanol, propanol, butanol and cyclohexanol, ketones such ascyclohexanone, or strongly polar solvents, e.g. amines such asN-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions, thesubstrates, either as such or dissolved in an oil or solvent, can behomogenized in water by means of a wetting agent, tackifier, dispersantor emulsifier. Alternatively, it is possible to prepare concentratescomprising active substance, wetting agent, tackifier, dispersant oremulsifier and, if desired, solvent or oil, which are suitable fordilution with water.

Suitable surfactants (adjuvants) are the alkali metal salts, alkalineearth metal salts and ammonium salts of aromatic sulfonic acids, e.g.ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, andof fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, laurylether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-,hepta- and octadecanols, and also of fatty alcohol glycol ethers,condensates of sulfonated naphthalene and its derivatives withformaldehyde, condensates of naphthalene, or of the naphthalenesulfonicacids with phenol and formaldehyde, polyoxyethylene octylphenol ether,ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl ortributylphenyl polyglycol ether, alkylaryl polyether alcohols,isotridecyl alcohol, fatty alcohol/ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylenealkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters,lignosulfite waste liquors or methylcellulose.

Powders, materials for broadcasting and dusts can be prepared by mixingor grinding the active substances together with a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneousgranules, can be prepared by binding the active compounds to solidcarriers. Solid carriers are mineral earths, such as silicas, silicagels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess,clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate,magnesium oxide, ground synthetic materials, fertilizers such asammonium sulfate, ammonium phosphate and ammonium nitrate, ureas, andproducts of vegetable origin, such as cereal meal, tree bark meal, woodmeal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the compounds of the formula I in the ready-to-usepreparations can be varied within wide ranges. In general, theformulations comprise from about 0.001 to 98% by weight, preferably 0.01to 95% by weight, of at least one active compound. The active compoundsare employed in a purity of from 90% to 100%, preferably 95% to 100%(according to the NMR spectrum).

The formulation examples below illustrate the production of suchpreparations:

-   -   I 20 parts by weight of an active compound of the formula I are        dissolved in a mixture composed of 80 parts by weight of        alkylated benzene, 10 parts by weight of the adduct of 8 to 10        mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide,        5 parts by weight of calcium dodecylbenzenesulfonate and 5 parts        by weight of the adduct of 40 mol of ethylene oxide to 1 mol of        castor oil. Pouring the solution into 100,000 parts by weight of        water and finely distributing it therein gives an aqueous        dispersion which comprises 0.02% by weight of the active        compound of the formula I.    -   II 20 parts by weight of an active compound of the formula I are        dissolved in a mixture composed of 40 parts by weight of        cyclohexanone, 30 parts by weight of isobutanol, 20 parts by        weight of the adduct of 7 mol of ethylene oxide to 1 mol of        isooctylphenol and 10 parts by weight of the adduct of 40 mol of        ethylene oxide to 1 mol of castor oil. Pouring the solution into        100,000 parts by weight of water and finely distributing it        therein gives an aqueous dispersion which comprises 0.02% by        weight of the active compound of the formula I.    -   III 20 parts by weight of an active compound of the formula I        are dissolved in a mixture composed of 25 parts by weight of        cyclohexanone, 65 parts by weight of a mineral oil fraction of        boiling point 210 to 280° C. and 10 parts by weight of the        adduct of 40 mol of ethylene oxide to 1 mol of castor oil.        Pouring the solution into 100,000 parts by weight of water and        finely distributing it therein gives an aqueous dispersion which        comprises 0.02% by weight of the active compound of the formula        I.    -   IV 20 parts by weight of an active compound of the formula I are        mixed thoroughly with 3 parts by weight of sodium        diisobutylnaphthalene sulfonate, 17 parts by weight of the        sodium salt of a lignosulfonic acid from a sulfite waste liquor        and 60 parts by weight of pulverulent silica gel, and the        mixture is ground in a hammer mill. Finely distributing the        mixture in 20,000 parts by weight of water gives a spray mixture        which comprises 0.1% by weight of the active compound of the        formula I.    -   V 3 parts by weight of an active compound of the formula I are        mixed with 97 parts by weight of finely divided kaolin. This        gives a dust which comprises 3% by weight of the active compound        of the formula I.    -   VI 20 parts by weight of an active compound of the formula I are        mixed intimately with 2 parts by weight of calcium        dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol        polyglycol ether, 2 parts by weight of the sodium salt of a        phenol/urea/formaldehyde condensate and 68 parts by weight of a        paraffinic mineral oil. This gives a stable oily dispersion.    -   VII 1 part by weight of an active compound of the formula I is        dissolved in a mixture composed of 70 parts by weight of        cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol        and 10 parts by weight of ethoxylated castor oil. This gives a        stable emulsion concentrate.    -   VIII 1 part by weight of an active compound of the formula I is        dissolved in a mixture composed of 80 parts by weight of        cyclohexanone and 20 parts by weight of Wettol^(R) EM 31        (=nonionic emulsifier based on ethoxylated castor oil). This        gives a stable emulsion concentrate.

The herbicidal compositions or the compounds of the formula I can beapplied pre- or post-emergence. If the active compounds are less welltolerated by certain crop plants, application techniques may be used inwhich the herbicidal compositions are sprayed, with the aid of thespraying equipment, in such a way that they come into contact as littleas possible, if at all, with the leaves of the sensitive crop plants,while the active compounds reach the leaves of undesirable plantsgrowing underneath, or the bare soil surface (post-directed, lay-by).

The application rates of the compound of the formula I are from 0.001 to3.0, preferably 0.01 to 1.0 kg/ha of active substance (a.s.), dependingon the control target, the season, the target plants and the growthstage.

To widen the activity spectrum and to achieve synergistic effects, thebenzenesulfonamide derivatives of the formula I may be mixed with alarge number of representatives of other herbicidal or growth-regulatingactive compound groups and then applied concomitantly. Suitablecomponents for mixtures are, for example, 1,2,4-thiadiazoles,1,3,4thiadiazoles, amides, aminophosphoric acid and its derivatives,aminotriazoles, anilides, (het)aryloxyalkanoic acids and theirderivatives, benzoic acid and its derivatives, benzothiadiazinones,2-hetaroyl/aroyl-1,3-cyclohexanediones, hetaryl aryl ketones,benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates,quinolinecarboxylic acid and its derivatives, chloroacetanilides,cyclohexenone oxime ether derivatives, diazines, dichloropropionic acidand its derivatives, dihydrobenzofurans, dihydrofuran-3-ones,dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls,halocarboxylic acids and their derivatives, ureas, 3-phenyluracils,imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides,oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionicesters, phenylacetic acid and its derivatives, 2-phenyl-propionic acidand its derivatives, pyrazoles, phenylpyrazoles, pyridazines,pyridinecarboxylic acid and its derivatives, pyrimidyl ethers,sulfonamides, sulfonylureas, triazines, triazinones, triazolinones,triazolecarboxamides and uracils.

It may furthermore be advantageous to apply the compounds of the formulaI, alone or else concomitantly in combination with other herbicides, inthe form of a mixture with other crop protection agents, for exampletogether with agents for controlling pests or phytopathogenic fungi orbacteria. Also of interest is the miscibility with mineral saltsolutions, which are employed for treating nutritional and trace elementdeficiencies. Non-phytotoxic oils and oil concentrates may also beadded.

USE EXAMPLES Herbicidal Efficacy

The herbicidal activity of the benzenesulfonamide derivatives of theformula I was demonstrated by the following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamysand with approximately 3.0% of humus as the substrate. The seeds of thetest plants were sown separately for each species.

For the pre-emergence treatment, the active compounds, emulsified orsuspended in water, were applied directly after sowing by means offinely distributing nozzles. The containers were irrigated gently topromote germination and growth and subsequently covered with transparentplastic hoods until the plants had rooted. This cover caused uniformgermination of the test plants, unless this was adversely affected bythe active compounds.

For the post-emergence treatment, the test plants were first grown to aheight of 3 to 15 cm, depending on the plant form, and only then treatedwith the active compounds, emulsified or suspended in water. The testplants were for this purpose either sown directly and grown in the samecontainers, or they were first grown separately as seedlings andtransplanted into the test containers a few days prior to treatment.

The application rate for the pre- and post-emergence treatment was from62.5 to 3.1 g of a.s./ha.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C.The test period extended over 2 to 4 weeks. During this time, the plantswere tended, and their response to the individual treatments wasevaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least theabove-ground parts, and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments were composed of thefollowing species: Scientific Name Common Name Abutilon theophrastiVelvet leaf Amaranthus retroflexus Pigweed Chenopodium album Commonlambsquarters Commelina benghalensis Bengal commelina Galium aparineCleavers harrif Ipomoea hederacea Morning glory Pharbitis purpureaCommon morning glory Polygonum convolvulus Wild buckwheat Polygonumpersicaria Ladysthumb Solanum nigrum Common nightshade

At application rates of 12.5 and 6.2 g/ha, the compounds 3.1 and 3.18(Table 3) showed very good pre-emergence activity against the unwantedplants pigweed, common lambsquarters, common morning glory and wildbuckwheat.

Furthermore, compounds 3.24 (Table 3) and 4.16 (Table 4), when appliedby the pre-emergence method at application rates of 6.2 and 3.1 g/ha,effected very good control of the unwanted plants velvet leaf, pigweed,common lambsquarters and morning glory.

The effectiveness of compound 3.32 (Table 3), when applied by thepre-emergence method at application rates of 62.5 and 31.2 g/ha, wasvery good against the unwanted plants velvet leaf, pigweed, commonlambsquarters and common nightshade.

At application rates of 15.6 and 7.8 g/ha, the compounds 3.27, 3.19,3.20 and 3.22 (Table 3) showed very good post-emergence activity againstthe unwanted plants pigweed, common lambsquarters, common morning gloryand ladysthumb.

Furthermore, compounds 2.29 (Table 2) and 3.26 (Table 3), when appliedby the post-emergence method at application rates of 15.6 and 7.8 g/ha,effected very good control of the unwanted plants pigweed, commonlambsquarters and common morning glory.

The effectiveness of compound 3.42 (Table 3), when applied by thepost-emergence method at application rates of 15.63 g/ha, was very goodagainst the unwanted plants velvet leaf, common morning glory andladiesthumb.

At application rates of 15.63 g/ha, the compounds 3.41 (Table 3) and4.14 (Table 4) showed very good post-emergence activity against theunwanted plants pigweed, cleavers harrif and ladiesthumb.

Furthermore, compound 2.17 (Table 2), when applied by the post-emergencemethod at application rates of 15.63 g/ha, effected very good control ofthe unwanted plants velvet leaf, common lambsquarters and Bengalcommelina.

The effectiveness of compound 2.28 (Table 2), when applied by thepost-emergence method at application rates of 15.63 g/ha, was very goodagainst the unwanted plants pigweed, common lambsquarters and commonmorning glory.

At application rates of 15.63 g/ha, the compound 2.27 (Table 2) showedvery good post-emergence activity against the unwanted plants pigweedand common morning glory.

USE EXAMPLES Desiccant/Defoliant Efficacy

The test plants used were young 4-leaf cotton plants (withoutcotyledons) which were grown under greenhouse conditions (rel.atmospheric humidity 50 to 70%; day/night temperature 27/20° C.).

The leaves of the young cotton plants were sprayed to runoff point withaqueous preparations of the active compounds (with addition of 0. 15% byweight of the fatty alcohol alkoxylate Plurafac® LF 700¹⁾, based on thespray liquor). The amount of water applied was 1000 l/ha (converted).After 13 days, the number of leaves that had been shed and the degree ofdefoliation in % were determined.¹⁾ A low-foam nonionic surfactant from BASF AG

The untreated control plants did not lose any leaves.

1-15. (canceled)
 16. A compound which is a benzenesulfonamide derivativeof the formula I

in which the variables are as defined below: X¹ is hydrogen or halogen;X² is chlorine; X³ is hydrogen, cyano, C₁-C₆-alkyl,C₁-C₆-alkoxy-C₁-C₄-alkyl, C₃-C₇-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynylor phenyl-C₁-C₄-alkyl, where the phenyl radical for its part may bepartially or fully halogenated and/or substituted by one to threeradicals selected from the group consisting of C₁-C₆-alkyl andC₁-C₆-alkoxy; Y is a group —C(A)B; A is oxygen; B is oxygen or sulfur;R¹ is hydrogen, halogen, hydroxyl, C₁-C₈-alkyl, C₃-C₇-cycloalkyl,C₃-C₇-cycloalkyl-C₁-C₄-alkyl, C₂-C₈-alkenyl, C₅-C₇-cycloalkenyl,C₃-C₈-alkynyl, C₁-C₈-alkoxy, C₃-C₇-cycloalkyloxy, C₂-C₈-alkenyloxy,C₃-C₈-alkynyloxy, aryl, aryloxy, aryl-C₁-C₄-alkyl; where the 13 lastmentioned radicals for their part may be partially or fully halogenatedand/or may carry one to three substituents selected from the groupconsisting of cyano, NO₂, hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₃-C₇-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-alkynyloxy, C₁-C₆-alkylthio,C₁-C₆-haloalkylthio, amino, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino,C₁-C₆-alkylsulfinyl, C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkylsulfonyl, C₁-C₆-alkoxysulfonyl, formyl,C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl, C₂-C₆-alkenylcarbonyl,C₃-C₆-alkynylcarbonyl, carboxy, C₁-C₆-alkoxycarbonyl,C₁-C₆-haloalkoxycarbonyl, C₂-C₆-alkenyloxycarbonyl,C₃-C₆-alkynyloxycarbonyl, mercaptocarbonyl, C₁-C₆-alkylthiocarbonyl,C₁-C₆-haloalkylthiocarbonyl, C₂-C₆-alkenylthiocarbonyl,C₃-C₆-alkynylthiocarbonyl, aminocarbonyl, C₁-C₆-alkylaminocarbonyl,di(C₁-C₆-alkylamino)carbonyl, C₁-C₆-haloalkylaminocarbonyl,di(C₁-C₆-haloalkylamino)carbonyl, C₂-C₆-alkenylaminocarbonyl,di(C₂-C₆-alkenylamino)carbonyl, C₃-C₆-alkynylaminocarbonyl,di(C₃-C₆-alkynylamino)carbonyl, phenyl, phenoxy, phenyl-C₁-C₄-alkyl andphenyl-C₁-C₄-alkoxy; four- to six-membered heterocyclyl which may bepartially or fully halogenated and/or substituted by one to threeradicals selected from the group consisting of C₁-C₆-alkyl andC₁-C₆-alkoxy; or four- to six-membered heterocyclyl-C₁-C₄-alkyl whichmay be partially or fully halogenated and/or substituted by one to threeradicals selected from the group consisting of C₁-C₆-alkyl andC₁-C₆-alkoxy; or five- or six-membered heteroaryl having one to fournitrogen atoms or having one to three nitrogen atoms and one oxygen orone sulfur atom or having one oxygen or sulfur atom, which radical maybe partially or fully halogenated and/or substituted by one to threeradicals selected from the group consisting of C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, amino, C₁-C₆-alkylaminoand di(C₁-C₆-alkyl)amino; or five- or six-memberedheteroaryl-C₁-C₄-alkyl having one to four nitrogen atoms or having oneto three nitrogen atoms and one oxygen or one sulfur atom or having oneoxygen or sulfur atom, which radical may be partially or fullyhalogenated and/or substituted by one to three radicals selected fromthe group consisting of C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, amino, C₁-C₆-alkylamino and di(C₁-C₆-alkyl)amino; R²is hydrogen, C₁-C₈-alkyl, C₂-C₈-alkenyl, C₃-C₈-alkynyl,C₃-C₇-cycloalkyl, where the four last mentioned radicals may bepartially or fully halogenated; or R¹ and R² together with the nitrogenatom to which they are attached form a three- to seven-memberedheterocycle which for its part may be partially or fully halogenatedand/or substituted by one to three radicals selected from the groupconsisting of C₁-C₆-alkyl, C₁-C₆-haloalkyl and C₁-C₆-alkoxy; Q is aradical selected from the group consisting of Q¹ to Q³⁹

A¹ to A¹⁷ are oxygen or sulfur; R³, R⁴, R⁷, R⁸, R¹¹, R¹², R¹⁸, R¹⁹, R²⁷,R²⁹, R³², R³³, R³⁸, R³⁹, R⁴⁴, R⁴⁵, R⁴⁶ and R⁴⁷ are hydrogen, cyano,hydroxyl, C₁-C₆-alkyl, C₁-C₆-cyanoalkyl, C₁-C₆-haloalkyl,C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyloxy, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkenyloxy, C₃-C₆-alkynyl,C₃-C₆-alkynyloxy, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,phenyl-C₁-C₆-alkyl, amino, C₁-C₆-alkylamino or di(C₁-C₆-alkyl)amino; orR³ and R⁴, R¹¹ and R¹², R¹⁸ and R¹⁹, or R⁴⁶ and R⁴⁷ together with theatoms to which they are attached form a three- to seven-memberedheterocycle which for its part may be partially or fully halogenatedand/or substituted by one to three radicals selected from the groupconsisting of C₁-C₆-alkyl and C₁-C₆-alkoxy; R⁵, R⁶, R⁹, R¹⁰, R¹⁵, R¹⁶,R²⁰, R²¹, R³⁰, R³¹, R³⁵, R³⁶, R⁴¹ and R⁴³ are hydrogen, hydroxyl,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyloxy,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,C₂-C₆-alkenyloxy, C₃-C₆-alkynyl, C₃-C₆-alkynyloxy, C₁-C₆-alkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-alkoxysulfonyl,C₁-C₆-alkylsulfonyloxy, amino, C₁-C₆-alkylamino or di(C₁-C₆-alkyl)amino;or R⁵ and R⁶, R⁹ and R¹⁰, R¹⁵ and R¹⁶, R²⁰ and R²¹, or R³⁰ and R³¹together with the atoms to which they are attached form a three- toseven-membered heterocycle which for its part may be partially or fullyhalogenated and/or substituted by one to three radicals selected fromthe group consisting of C₁-C₆-alkyl and C₁-C₆-alkoxy; R¹³, R¹⁴, R²²,R²³, R²⁵ and R²⁶ are hydrogen, halogen or C₁-C₆-alkyl; R¹⁷, R²⁸, R³⁴,R³⁷ and R⁴⁰ are hydrogen, halogen, hydroxyl, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyloxy, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₂-C₆-alkenyl,C₂-C₆-haloalkenyl, C₂-C₆-alkenyloxy, C₃-C₆-alkynyl or C₃-C₆-alkynyloxy;R²⁴ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl,C₃-C₆-alkynyl, C₁-C₆-haloalkoxy, amino, C₁-C₆-alkylamino ordi(C₁-C₆-alkyl)amino; or an agriculturally useful salt thereof.
 17. Acompound of claim 16, in which X¹ is hydrogen, fluorine or chlorine. 18.A compound of claim 16, in which Q is Q¹, Q², Q⁵, Q⁷, Q⁸, Q¹⁰, Q¹², Q¹³,Q¹⁷, Q²⁰, Q²¹, Q²², Q²³, Q²⁴, Q²⁷, Q³¹, Q³², Q³⁴, Q³⁸ or Q³⁹.
 19. Acompound of claim 16, in which Q is Q⁷, Q²¹, Q²², Q²⁷, Q³², Q³⁸ or Q³⁹.20. A process for preparing a compound of claim 16, where X³ ishydrogen, which comprises reacting a benzenesulfonyl iso(thio)cyanate ofthe formula II

where X¹, X², A and Q are as defined in claim 16, with an amine of theformula III or an alcohol or thiol of the formula IVwhere B=NR²   IIIHBR¹where B=O, S   IV where R¹ and R² are as defined in claim
 16. 21. Abenzenesulfonyl iso(thio)cyanate of the formula II

where X¹, X², A and Q are as defined in claim
 16. 22. A compositioncomprising a herbicidally effective amount of at least onebenzenesulfonamide derivative of the formula I or an agriculturallyuseful salt of I according to claim 16 and auxiliaries customary forformulating crop protection agents.
 23. A composition for thedesiccation and/or defoliation of plants, comprising such an amount ofat least one benzenesulfonamide derivative of the formula I or anagriculturally useful salt of I according to claim 16 that acts as adesiccant and/or defoliant, and auxiliaries customary for formulatingcrop protection agents.
 24. A process for preparing herbicidallyeffective compositions, which comprises mixing a herbicidally effectiveamount of at least one benzenesulfonamide derivative of the formula I oran agriculturally useful salt of I according to claim 16 and auxiliariescustomary for formulating crop protection agents.
 25. A process forpreparing compositions having desiccant and/or defoliant action, whichcomprises mixing a desiccant and/or defoliant effective amount of atleast one compound according to claim 16 and auxiliaries customary forformulating crop protection agents.
 26. A method for controllingunwanted vegetation, wherein a herbicidally effective amount of at leastone benzenesulfonamide derivative of the formula I or an agriculturallyuseful salt of I according to claim 16 is allowed to act on the unwantedvegetation, their habitat and/or on their seeds.
 27. A method for thedesiccation and/or defoliation of plants, which comprises allowing adesiccant and/or defoliant effective amount of at least one compoundaccording to claim 16 to act on the plants.
 28. A compound of claim 16,wherein the compound is a compound of formulae I.2.1 to I.2.689.
 29. Acompound of claim 16, wherein the compound is a compound of formulaeI.3.1 to I.3.689.
 30. A compound of claim 16, wherein the compound is acompound of formulae I.8.1 to I.8.689.
 31. A compound of claim 16,wherein the compound is a compound of formulae I.9.1 to I.9.689.
 32. Acompound of claim 16, wherein the compound is a compound of formulaeI.14.1 to I.14.689.
 33. A compound of claim 16, wherein the compound isa compound of formulae I.15.1 to I.15.689.
 34. A compound of claim 16,wherein the compound is a compound of formulae I.20.1 to I.20.689.
 35. Acompound of claim 16, wherein the compound is a compound of formulaeI.21.1 to I.21.689.
 36. A compound of claim 16, wherein the compound isa compound of formulae I.26.1 to I.26.689.
 37. A compound of claim 16,wherein the compound is a compound of formulae I.27.1 to I.27.689.
 38. Acompound of claim 16, wherein the compound is a compound of formulaeI.32.1 to I.32.689.
 39. A compound of claim 16, wherein the compound isa compound of formulae I.33.1 to I.33.689.